Cyclopentanone → 3-Cyclopentylamino-2,2-dimethyl-propanoic acid methyl ester

HRID 2111256노트

반응식

HRID 2111256 반응식
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][NH2:6].[C:10]1(=O)[CH2:14][CH2:13][CH2:12][CH2:11]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][NH:6][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1

참가 물질

6

반응물 4

HCID 8452CyclopentanoneHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 13285789Methyl 3-amino-2,2-dimethylpropanoate

생성물 1

HCID 576350433-Cyclopentylamino-2,2-dimethyl-propanoic acid methyl ester수율 95.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 21.98 g (0.167 mole) of 3-amino-2,2-dimethyl-propanoic acid methyl ester (from method 6) in 500 mL of dichloromethane cooled to 0 degrees, was added 14.1 g (0.167 mole) of cyclopentanone, 16.0 g (0.181 mole) of sodium acetate and 52.0 g (0.025 mole) of sodium triacetoxyborohydride. The mixture stirred at room temp. for 22 hours, and then quenched by the addition of 500 mL of saturated sodium bicarbonate solution. The mixture was stirred for 1 hour and then extracted twice 400 mL of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 31.8 g of 3-cyclopentylamino-2,2-dimethyl-propanoic acid methyl ester which was used without further purification.

후처리

  1. customquenched by the addition of 500 mL of saturated sodium bicarbonate solution
  2. stirringThe mixture was stirred for 1 hour
  3. extractionextracted twice 400 mL of dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2bf9a22d74014e8a8d07086cc1a588d1
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517873B2

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