Imidazole → (R)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

HRID 497075

反応式

HRID 497075 の反応式
N1C=CN=C1.[OH:6][CH2:7][C@@H:8]1[NH:12][C:11](=[O:13])[CH2:10][CH2:9]1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl>[Si:14]([O:6][CH2:7][C@@H:8]1[NH:12][C:11](=[O:13])[CH2:10][CH2:9]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone

生成物 1

HCID 13771167(R)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one収率 115.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Imidazole (5.24 g, 77 mmols) was added to a CH2Cl2 (85 ml) solution of (5R)-5-(hydroxymethyl)-2-pyrrolidinone (4.03 g, 35 mmols). Then, during cooling with ice, a CH2Cl2 (15 ml) solution of tert-butyldimethylsilyl chloride (4.53 g, 30 mmols) was added, and the mixture was stirred for 15 hours at room temperature. The solvent was distilled off under reduced pressure, and then the residue was subjected to silica gel column chromatography (SiO2 300 g, MeOH—CHCl3 5:95 v/v) to obtain (5R)-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidin-2-one (7.92 g, 98.7%):

後処理

  1. temperatureThen, during cooling with ice
  2. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-15a1ecbc71dc4a95a037f2d5cec9f155
出典データセット
uspto-grants-2005_09
特許番号
US06949553B2

関連ノート

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