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

HRID 72201

反応式

HRID 72201 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-727bc034e03f46d881500135dc23264a
出典データセット
uspto-grants-2014_09
特許番号
US08828991B2

関連ノート

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