(1R,2S)-2-amino-2,3-dihydro-1H-inden-1-ol

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

実験手順: The title compound was prepared in a similar manner to Example 26 from (±) cis 2-amino-1-indanol (2.24 g, 15.0 mmol), sodium hydride (0.54 g of an 80% dispersion in oil; 18.0 mmol) and 1,2-dichloro-4-fluorobenzene (2.97 g, 18.0 mmol). The crude product was purified by chromatography on silica eluting with 0-4% ethanol in diethyl ether. The resulting light brown oil (3.89 g) was extracted into a mixture of hexane and diethyl ether and treated with ethereal HCl to give the hydrochloride salt. Recrystallisation afforded the title compound as a colourless solid, m.p. 214°-215° C. (dec) (from methanol/ethyl acetate/diethyl ether). The crude product was purified by chromatography on silica eluting with 0-4% ethanol in diethyl ether The resulting light brown oil (3.89 g) was extracted into a mixture of hexane and diethyl ether treated with ethereal HCl

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

実験手順: A suspension of (±) cis 3,3a,4,8b-tetrahydroindeno[2,1 -d]oxazol-2-one (Preparation 27) (5.73 g, 0.033 mol) in a mixture of ethanol (100 ml) and water (20 ml) was treated with sodium hydroxide pellets (8.0 g, 0.2 mol). After stirring at room temperature until the sodium hyroxide pellets had dissolved the mixture was heated under reflux in an argon atmosphere for 5 h. The solution was concentrated in vacuo to approximately one quarter the original volume then diluted with brine (50 ml) and extracted into chloroform (3×100 ml). The combined organic extracts were dried over Na2SO4 and then concentrated in vacuo to give a brown solid (4.74 g) which was crystallised from i-propanol-diethyl ether to give the title compound as a colourless solid (3.5 g, 72%) m.p. 104.5°-106° C. Mother liquors afforded a further 0.41 g, m.p. 103.5°-105° C. had dissolved the mixture was heated under reflux in an argon atmosphere for 5 h The solution was concentrated in vacuo to approximately one quarter the original volume then diluted with brine (50 ml) extracted into chloroform (3×100 ml) The combined organic extracts were dried over Na2SO4 concentrated in vacuo

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

実験手順: A suspension of (±) cis 3,3a,4,8b-tetrahydroindeno[2,1 -d]oxazol-2-one (Preparation 27) (5.73 g, 0.033 mol) in a mixture of ethanol (100 ml) and water (20 ml) was treated with sodium hydroxide pellets (8.0 g, 0.2 mol). After stirring at room temperature until the sodium hyroxide pellets had dissolved the mixture was heated under reflux in an argon atmosphere for 5 h. The solution was concentrated in vacuo to approximately one quarter the original volume then diluted with brine (50 ml) and extracted into chloroform (3×100 ml). The combined organic extracts were dried over Na2SO4 and then concentrated in vacuo to give a brown solid (4.74 g) which was crystallised from i-propanol-diethyl ether to give the title compound as a colourless solid (3.5 g, 72%) m.p. 104.5°-106° C. Mother liquors afforded a further 0.41 g, m.p. 103.5°-105° C. had dissolved the mixture was heated under reflux in an argon atmosphere for 5 h The solution was concentrated in vacuo to approximately one quarter the original volume then diluted with brine (50 ml) extracted into chloroform (3×100 ml) The combined organic extracts were dried over Na2SO4 concentrated in vacuo

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

実験手順: The title compound was prepared in a similar manner to Example 26 from (±) cis 2-amino-1-indanol (2.24 g, 15.0 mmol), sodium hydride (0.54 g of an 80% dispersion in oil; 18.0 mmol) and 1,2-dichloro-4-fluorobenzene (2.97 g, 18.0 mmol). The crude product was purified by chromatography on silica eluting with 0-4% ethanol in diethyl ether. The resulting light brown oil (3.89 g) was extracted into a mixture of hexane and diethyl ether and treated with ethereal HCl to give the hydrochloride salt. Recrystallisation afforded the title compound as a colourless solid, m.p. 214°-215° C. (dec) (from methanol/ethyl acetate/diethyl ether). The crude product was purified by chromatography on silica eluting with 0-4% ethanol in diethyl ether The resulting light brown oil (3.89 g) was extracted into a mixture of hexane and diethyl ether treated with ethereal HCl

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

実験手順: A suspension of (±) cis 3,3a,4,8b-tetrahydroindeno[2,1 -d]oxazol-2-one (Preparation 27) (5.73 g, 0.033 mol) in a mixture of ethanol (100 ml) and water (20 ml) was treated with sodium hydroxide pellets (8.0 g, 0.2 mol). After stirring at room temperature until the sodium hyroxide pellets had dissolved the mixture was heated under reflux in an argon atmosphere for 5 h. The solution was concentrated in vacuo to approximately one quarter the original volume then diluted with brine (50 ml) and extracted into chloroform (3×100 ml). The combined organic extracts were dried over Na2SO4 and then concentrated in vacuo to give a brown solid (4.74 g) which was crystallised from i-propanol-diethyl ether to give the title compound as a colourless solid (3.5 g, 72%) m.p. 104.5°-106° C. Mother liquors afforded a further 0.41 g, m.p. 103.5°-105° C. had dissolved the mixture was heated under reflux in an argon atmosphere for 5 h The solution was concentrated in vacuo to approximately one quarter the original volume then diluted with brine (50 ml) extracted into chloroform (3×100 ml) The combined organic extracts were dried over Na2SO4 concentrated in vacuo