Pyridine → Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

HRID 72201

반응식

HRID 72201 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].N1C=CC=CC=1.C(OCC)(=O)C>ClCCl.O>[C:6]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C@@H:15]([O:18][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 10934372Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

Methanesulfonyl chloride was added to a mixture of (S)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (40 g) and pyridine (17.4 g) in dichloromethane (400 mL) at 0° C. The reaction mixture was stirred at this temperature for 15 min and then heated at 50° C. for 8 h. The reaction mixture was subsequently mixed with ethyl acetate and water, and the ethyl acetate phase was washed with dil. HCl solution. The ethyl acetate phase was dried over sodium sulfate and the solvent was removed in vacuo. The (R)-3-methanesulfonyloxypyrrolidine-1-carboxylic acid tert-butyl ester obtained in this way was dissolved in pyrrolidine (18.2 mL), and the reaction mixture was heated to 100° C. The reaction mixture was then mixed with ethyl acetate and water. The ethyl acetate phase was washed several times with water. The organic phase was dried over sodium sulfate and the solvent was removed in vacuo.

후처리

  1. washthe ethyl acetate phase was washed with dil. HCl solution
  2. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  3. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-727bc034e03f46d881500135dc23264a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828991B2

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