TERT-BUTYL 4-HYDROXYBUTYLMETHYLCARBAMATE

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 250 mL round bottom flask, charged with 3.00 g (28.5 mmol) of N-methyl-4-aminobutanol in 75 mL of dioxane, was added 5 mL of triethylamine (35.4 mmol) followed by 7.85 g (31.9 mmol) of BOC-ON, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile. The mixture was stirred at room temperature for 20 h and then concentrated via rotary evaporation. The residue was chromatographed on silica gel, eluting first with 20% ethyl acetate/hexane, then with 40% ethyl acetate/hexane, and finally with 75% ethyl/hexane. The fractions containing product were combined and concentrated via rotary evaporation to afford 4.85 g of the product (32) as a near colorless oil (84%): 1H-NMR (CDCl3) d 3.65 (2H, t), 3.23 (2H, t), 2.81 (3H, s), 1.67-1.45 (4H, m), and 1.42 (9H, s) ppm. concentrated via rotary evaporation The residue was chromatographed on silica gel eluting first with 20% ethyl acetate/hexane The fractions containing product concentrated via rotary evaporation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred and cooled (<10° C.) solution of 150 parts of pyridinium dichromate in 1300 parts of dichloromethane was added dropwise a solution of 50 parts of (1,1-dimethylethyl) (4-hydroxybutyl)methylcarbamate in 91 parts of dichloromethane. Upon complete addition, stirring was continued for 3 hours in the presence of 112 parts of molecular sieves of 4A at room temperature. The reaction mixture was filtered over magnesium sulfate, washed with 1,1'-oxydisethane and the filtreate was evaporated. The residue was purified by column chromatography over silica gel using dichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was taken up in methylbenzene and the whole was evaporated again, yielding 3.5 parts (6.9%) of (1,1-dimethylethyl) (methyl(4-oxobutyl)carbamate as a residue (interm. 7). Upon complete addition stirring The reaction mixture was filtered over magnesium sulfate washed with 1,1'-oxydisethane the filtreate was evaporated The residue was purified by column chromatography over silica gel The pure fractions were collected the eluent was evaporated the whole was evaporated again

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred and cooled (<10° C.) solution of 150 parts of pyridinium dichromate in 1300 parts of dichloromethane was added dropwise a solution of 50 parts of (1,1-dimethylethyl) (4-hydroxybutyl)methylcarbamate in 91 parts of dichloromethane. Upon complete addition, stirring was continued for 3 hours in the presence of 112 parts of molecular sieves of 4A at room temperature. The reaction mixture was filtered over magnesium sulfate, washed with 1,1'-oxydisethane and the filtreate was evaporated. The residue was purified by column chromatography over silica gel using dichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was taken up in methylbenzene and the whole was evaporated again, yielding 3.5 parts (6.9%) of (1,1-dimethylethyl) (methyl(4-oxobutyl)carbamate as a residue (interm. 7). Upon complete addition stirring The reaction mixture was filtered over magnesium sulfate washed with 1,1'-oxydisethane the filtreate was evaporated The residue was purified by column chromatography over silica gel The pure fractions were collected the eluent was evaporated the whole was evaporated again

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 250 mL round bottom flask, charged with 3.00 g (28.5 mmol) of N-methyl-4-aminobutanol in 75 mL of dioxane, was added 5 mL of triethylamine (35.4 mmol) followed by 7.85 g (31.9 mmol) of BOC-ON, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile. The mixture was stirred at room temperature for 20 h and then concentrated via rotary evaporation. The residue was chromatographed on silica gel, eluting first with 20% ethyl acetate/hexane, then with 40% ethyl acetate/hexane, and finally with 75% ethyl/hexane. The fractions containing product were combined and concentrated via rotary evaporation to afford 4.85 g of the product (32) as a near colorless oil (84%): 1H-NMR (CDCl3) d 3.65 (2H, t), 3.23 (2H, t), 2.81 (3H, s), 1.67-1.45 (4H, m), and 1.42 (9H, s) ppm. concentrated via rotary evaporation The residue was chromatographed on silica gel eluting first with 20% ethyl acetate/hexane The fractions containing product concentrated via rotary evaporation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 250 mL round bottom flask, charged with 3.00 g (28.5 mmol) of N-methyl-4-aminobutanol in 75 mL of dioxane, was added 5 mL of triethylamine (35.4 mmol) followed by 7.85 g (31.9 mmol) of BOC-ON, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile. The mixture was stirred at room temperature for 20 h and then concentrated via rotary evaporation. The residue was chromatographed on silica gel, eluting first with 20% ethyl acetate/hexane, then with 40% ethyl acetate/hexane, and finally with 75% ethyl/hexane. The fractions containing product were combined and concentrated via rotary evaporation to afford 4.85 g of the product (32) as a near colorless oil (84%): 1H-NMR (CDCl3) d 3.65 (2H, t), 3.23 (2H, t), 2.81 (3H, s), 1.67-1.45 (4H, m), and 1.42 (9H, s) ppm. concentrated via rotary evaporation The residue was chromatographed on silica gel eluting first with 20% ethyl acetate/hexane The fractions containing product concentrated via rotary evaporation

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 50 parts of (1,1-dimethylethyl) (4-hydroxybutyl)methylcarbamate in 91 parts of dichloromethane was added dropwise to a mixture of 150 parts of pyridinium dichromate, 112 parts of molecular sieves and 1300 parts of dichloromethane at a temperature about 10° C. Upon completion, stirring was continued for 3 hours at room temperature. The reaction mixture was filtered, washed with 1,1'-oxybisethane and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using dichloromethane as eluent. The pure fractions were collected and the eluent was evaporated with methylbenzene, yielding 35 parts (70%) of (1,1-dimethylethyl) methyl(4-oxobutyl)carbamate as a residue (int. 38). The reaction mixture was filtered washed with 1,1'-oxybisethane the filtrate was evaporated The residue was purified by column chromatography over silica gel The pure fractions were collected the eluent was evaporated with methylbenzene

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 50 parts of (1,1-dimethylethyl) (4-hydroxybutyl)methylcarbamate in 91 parts of dichloromethane was added dropwise to a mixture of 150 parts of pyridinium dichromate, 112 parts of molecular sieves and 1300 parts of dichloromethane at a temperature about 10° C. Upon completion, stirring was continued for 3 hours at room temperature. The reaction mixture was filtered, washed with 1,1'-oxybisethane and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using dichloromethane as eluent. The pure fractions were collected and the eluent was evaporated with methylbenzene, yielding 35 parts (70%) of (1,1-dimethylethyl) methyl(4-oxobutyl)carbamate as a residue (int. 38). The reaction mixture was filtered washed with 1,1'-oxybisethane the filtrate was evaporated The residue was purified by column chromatography over silica gel The pure fractions were collected the eluent was evaporated with methylbenzene

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred and cooled (<10° C.) solution of 150 parts of pyridinium dichromate in 1300 parts of dichloromethane was added dropwise a solution of 50 parts of (1,1-dimethylethyl) (4-hydroxybutyl)methylcarbamate in 91 parts of dichloromethane. Upon complete addition, stirring was continued for 3 hours in the presence of 112 parts of molecular sieves of 4A at room temperature. The reaction mixture was filtered over magnesium sulfate, washed with 1,1'-oxybisethane and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using dichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was taken up in methylbenzene and the whole was evaporated again, yielding 3.5 parts (6.9%) of (1,1-dimethylethyl) methyl(4-oxobutyl)carbamate as a residue (interm. 7). Upon complete addition stirring The reaction mixture was filtered over magnesium sulfate washed with 1,1'-oxybisethane the filtrate was evaporated The residue was purified by column chromatography over silica gel The pure fractions were collected the eluent was evaporated the whole was evaporated again

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 50 parts of (1,1-dimethylethyl) (4-hydroxybutyl)methylcarbamate in 91 parts of dichloromethane was added dropwise to a mixture of 150 parts of pyridinium dichromate, 112 parts of molecular sieves and 1300 parts of dichloromethane at a temperature about 10° C. Upon completion, stirring was continued for 3 hours at room temperature. The reaction mixture was filtered, washed with 1,1'-oxybisethane and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using dichloromethane as eluent. The pure fractions were collected and the eluent was evaporated with methylbenzene, yielding 35 parts (70%) of (1,1-dimethylethyl) methyl(4-oxobutyl)carbamate as a residue (int. 38). The reaction mixture was filtered washed with 1,1'-oxybisethane the filtrate was evaporated The residue was purified by column chromatography over silica gel The pure fractions were collected the eluent was evaporated with methylbenzene

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 250 mL round bottom flask, charged with 3.00 g (28.5 mmol) of N-methyl-4-aminobutanol in 75 mL of dioxane, was added 5 mL of triethylamine (35.4 mmol) followed by 7.85 g (31.9 mmol) of BOC-ON, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile. The mixture was stirred at room temperature for 20 h and then concentrated via rotary evaporation. The residue was chromatographed on silica gel, eluting first with 20% ethyl acetate/hexane, then with 40% ethyl acetate/hexane, and finally with 75% ethyl/hexane. The fractions containing product were combined and concentrated via rotary evaporation to afford 4.85 g of the product (32) as a near colorless oil (84%): 1H-NMR (CDCl3) d 3.65 (2H, t), 3.23 (2H, t), 2.81 (3H, s), 1.67-1.45 (4H, m), and 1.42 (9H, s) ppm. concentrated via rotary evaporation The residue was chromatographed on silica gel eluting first with 20% ethyl acetate/hexane The fractions containing product concentrated via rotary evaporation