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CC(C)(C)OC(=O)NNC1CCCC1製品情報
tert-butyl N-(cyclopentylamino)carbamate (CAS 646071-31-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
想定用途
専門的研究・工業用途限定
データベース ID 23113328
安全上の注意
For professional research and industrial use only. Review the supplier safety data sheet before handling.
合成データ
12 反応 · 12 文献
反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-6a91fba8b50c4b50aadcbee3c52ca39c反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: To a solution of 1-cyclopentylhydrazine-2-carboxylic acid tert-butyl ester (18.4 g, 92 mmol) in a mixture of ethanol (300 mL) and conc. HCl (7.7 mL, 92 mmol) was added ethyl 2-acetyl-3-(dimethylamino)acrylate (25.5 g, 0.138 mol). The resulting mixture was refluxed for 2 h. The reaction was concentrated in vacuo, dissolved in CH2Cl2 (300 mL), washed with satd NaHCO3, and brine, dried (Na2SO4), concentrated in vacuo and purified by chromatography on silica gel to give ethyl 1-cyclopentyl-5-methyl-1H-pyrazole-4-carboxylate (15.6 g, 76% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.15 (s, 1 H), 4.61 (m, 1 H), 4.15 (q, J=8 Hz, 2 H), 2.29 (s, 3 H), 2.04-1.97 (m, 2 H), 1.89-1.85 (m, 2 H), 1.78-1.71 (m, 2 H), 1.62-1.59 (m, 2 H), 1.23 (t, J=8 Hz, 3 H). The resulting mixture was refluxed for 2 h The reaction was concentrated in vacuo dissolved in CH2Cl2 (300 mL) washed with satd NaHCO3, and brine dried (Na2SO4) concentrated in vacuo purified by chromatography on silica gel
ソース ID: ord-ed0965a4082248eea0ca6171fa9d591c反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: To a solution of 1-cyclopentylhydrazine-2-carboxylic acid tert-butyl ester (18.4 g, 92 mmol) in a mixture of ethanol (300 mL) and conc. HCl (7.7 mL, 92 mmol) was added ethyl 2-acetyl-3-(dimethylamino)acrylate (25.5 g, 0.138 mol). The resulting mixture was refluxed for 2 h. The reaction was concentrated in vacuo, dissolved in CH2Cl2 (300 mL), washed with satd NaHCO3, and brine, dried (Na2SO4), concentrated in vacuo and purified by chromatography on silica gel to give ethyl 1-cyclopentyl-5-methyl-1H-pyrazole-4-carboxylate (15.6 g, 76% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.15 (s, 1 H), 4.61 (m, 1 H), 4.15 (q, J=8 Hz, 2 H), 2.29 (s, 3 H), 2.04-1.97 (m, 2 H), 1.89-1.85 (m, 2 H), 1.78-1.71 (m, 2 H), 1.62-1.59 (m, 2 H), 1.23 (t, J=8 Hz, 3 H). The resulting mixture was refluxed for 2 h The reaction was concentrated in vacuo dissolved in CH2Cl2 (300 mL) washed with satd NaHCO3, and brine dried (Na2SO4) concentrated in vacuo purified by chromatography on silica gel
ソース ID: ord-ed0965a4082248eea0ca6171fa9d591c反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Sodium cyanoborohydride (6.4 g, 0.101 mol) was added portion-wise to a suspension of 1-cyclopentylidenehydrazine-2-carboxylic acid tert-butyl ester (20 g, 0.101 mol) in a mixture of acetic acid and methanol (288 mL, 1:1). The resulting solution was stirred at RT for 2 h. The reaction mixture was neutralized with 1 N aq NaOH and extracted with CH2Cl2. The organic layer was washed with saturated NaHCO3, dried (Na2SO4) and concentrated under reduced pressure to give 1-cyclopentylhydrazine-2-carboxylic acid tert-butyl ester (18.4 g) as an oil. extracted with CH2Cl2 The organic layer was washed with saturated NaHCO3 dried (Na2SO4) concentrated under reduced pressure
ソース ID: ord-d241d90089c44fb5aaf2fcf740cb8fb0反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A mixture of 1,1,3,3-tetramethoxy-propane (13.6 g, 83 mmol) and 1-cyclopentylhydrazine-2-carboxylic acid tert-butyl ester from Ex B18 (16.6 g, 83 mmol) in water (150 mL) was treated with conc HCl (21 mL, 252 mmol) and the resulting mixture was heated at reflux overnight. The reaction mixture was allowed to cool to RT and was extracted with ether. The extracts were washed with brine, dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to give 1-cyclopentyl-1H-pyrazole (8.0 g, 71% yield). 1H NMR (400 MHz, CDCl3): δ 7.52 (s, 1 H), 7.43 (s, 1 H), 6.24 (s, 1 H), 4.68 (m, 1 H), 2.20-1.71 (m, 8 H); MS (ESI) m/z: 137.1 [M+H+] the resulting mixture was heated at reflux overnight was extracted with ether The extracts were washed with brine dried over anhydrous MgSO4 filtered The filtrate was concentrated in vacuo
ソース ID: ord-a05c708e2a44488e92bbbf8a814ced04反応条件: temp:67.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Cyclopentanone (5.000 g, 59.44 mmol; CAS #120-92-3, purchased from Aldrich) was dissolved in hexanes (90 mL). t-Butyl carbazate (7.860 g, 59.47 mmol) was added and the mixture was heated at 65-70° C. for 1 hour. The mixture was cooled and concentrated in vacuo. The residue was taken up in isopropanol (25 mL)-ether (25 mL)-hexanes (50 mL) and chilled. The crystalline material was collected by filtration to give N′-cyclopentyl-hydrazinecarboxylic acid tert-butyl ester (5.51 g; 47%). A second crop (2.62 g, 22%) was collected from the mother liquor. The mixture was cooled concentrated in vacuo chilled The crystalline material was collected by filtration
ソース ID: ord-a55d876453f4475cb4c8243c9b31c485反応条件: temp:67.51; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Cyclopentanone (5.000 g, 59.44 mmol; CAS #120-92-3, purchased from Aldrich) was dissolved in hexanes (90 mL). t-Butyl carbazate (7.860 g, 59.47 mmol) was added and the mixture was heated at 65-70° C. for 1 hour. The mixture was cooled and concentrated in vacuo. The residue was taken up in isopropanol (25 mL)-ether (25 mL)-hexanes (50 mL) and chilled. The crystalline material was collected by filtration to give N′-cyclopentyl-hydrazinecarboxylic acid tert-butyl ester (5.51 g; 47%). A second crop (2.62 g, 22%) was collected from the mother liquor. The mixture was cooled concentrated in vacuo chilled The crystalline material was collected by filtration
ソース ID: ord-a55d876453f4475cb4c8243c9b31c485反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-6a91fba8b50c4b50aadcbee3c52ca39c反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A mixture of 1,1,3,3-tetramethoxypropane (13.6 g, 83 mmol) and N2-cyclopentyl-N1-(tert-butoxycarbonyl)hydrazine (16.6 g, 83 mmol, see Ranatunge et al., J. Med. Chem. (2004), 47, p2180-2193) in water (150 mL) was treated with cone. HCl (21 mL, 252 mmol). The resulting mixture was heated at reflux overnight. The completed reaction mixture was extracted with ether and the extracts were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo to give 1-cyclopentyl-1 H-pyrazole (8.0 g, 71% yield. 1H NMR (400 MHz, CDCl3): δ 7.52 (s, 1 H), 7.43 (s, 1 H), 6.24 (s, 1 H), 4.68 (m, 1 H), 2.20-1.71 (m, 8 H). MS (ESI) m/z; 137.1 [M+H+]. was treated with cone The resulting mixture was heated at reflux overnight The completed reaction mixture was extracted with ether the extracts were washed with brine dried over anhydrous MgSO4 concentrated in vacuo
ソース ID: ord-fea1f5478c13454b9fa6f77671454262反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: To a solution of 1-cyclopentylhydrazine-2-carboxylic acid tert-butyl ester (18.4 g, 92 mmol) in a mixture of ethanol (300 mL) and conc. HCl (7.7 mL, 92 mmol) was added ethyl 2-acetyl-3-(dimethylamino)acrylate (25.5 g, 0.138 mol). The resulting mixture was refluxed for 2 h. The reaction was concentrated in vacuo, dissolved in CH2Cl2 (300 mL), washed with satd NaHCO3, and brine, dried (Na2SO4), concentrated in vacuo and purified by chromatography on silica gel to give ethyl 1-cyclopentyl-5-methyl-1H-pyrazole-4-carboxylate (15.6 g, 76% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.15 (s, 1 H), 4.61 (m, 1 H), 4.15 (q, J=8 Hz, 2 H), 2.29 (s, 3 H), 2.04-1.97 (m, 2 H), 1.89-1.85 (m, 2 H), 1.78-1.71 (m, 2 H), 1.62-1.59 (m, 2 H), 1.23 (t, J=8 Hz, 3 H). The resulting mixture was refluxed for 2 h The reaction was concentrated in vacuo dissolved in CH2Cl2 (300 mL) washed with satd NaHCO3, and brine dried (Na2SO4) concentrated in vacuo purified by chromatography on silica gel
ソース ID: ord-ed0965a4082248eea0ca6171fa9d591c反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Sodium cyanoborohydride (6.4 g, 0.101 mol) was added portion-wise to a suspension of 1-cyclopentylidenehydrazine-2-carboxylic acid tert-butyl ester (20 g, 0.101 mol) in a mixture of acetic acid and methanol (288 mL, 1:1). The resulting solution was stirred at RT for 2 h. The reaction mixture was neutralized with 1 N aq NaOH and extracted with CH2Cl2. The organic layer was washed with saturated NaHCO3, dried (Na2SO4) and concentrated under reduced pressure to give 1-cyclopentylhydrazine-2-carboxylic acid tert-butyl ester (18.4 g) as an oil. extracted with CH2Cl2 The organic layer was washed with saturated NaHCO3 dried (Na2SO4) concentrated under reduced pressure
ソース ID: ord-d241d90089c44fb5aaf2fcf740cb8fb0反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A mixture of 1,1,3,3-tetramethoxy-propane (13.6 g, 83 mmol) and 1-cyclopentylhydrazine-2-carboxylic acid tert-butyl ester from Ex B18 (16.6 g, 83 mmol) in water (150 mL) was treated with conc HCl (21 mL, 252 mmol) and the resulting mixture was heated at reflux overnight. The reaction mixture was allowed to cool to RT and was extracted with ether. The extracts were washed with brine, dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to give 1-cyclopentyl-1H-pyrazole (8.0 g, 71% yield). 1H NMR (400 MHz, CDCl3): δ 7.52 (s, 1 H), 7.43 (s, 1 H), 6.24 (s, 1 H), 4.68 (m, 1 H), 2.20-1.71 (m, 8 H); MS (ESI) m/z: 137.1 [M+H+] the resulting mixture was heated at reflux overnight was extracted with ether The extracts were washed with brine dried over anhydrous MgSO4 filtered The filtrate was concentrated in vacuo
ソース ID: ord-a05c708e2a44488e92bbbf8a814ced04PubChem References
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