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

HRID 222448

反応式

HRID 222448 の反応式
[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C(OCC)(=O)C>CN(C)C=O.CCCCCC>[Si:14]([O:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

参加物

7

反応物 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 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 107.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8058Hexane溶媒

実験手順

Under atmosphere of argon, a solution of (5R)-5-hydroxymethylpyrollidin-2-one (10 g) and imidazole (8.8 g) in dry dimethylformamide (50 mL) was added by a solution of t-butyldimethylsilyl chloride (15.6 g) in dry dimethylformamide (50 mL) at room temperature, and the mixture was stirred for 5 hours. To the mixture, a mixed solvent of ethyl acetate and hexane was added. The diluted solution was washed with water and brine successively, dried over an anhydrous sodium sulfate, concentrated under reduced pressure to give the title compound (21.41 g) having the following physical data.

後処理

  1. washThe diluted solution was washed with water and brine successively
  2. dry with materialdried over an anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a03349e921f9436080d515cb9d94a4c2
出典データセット
uspto-grants-2012_06
特許番号
US08207223B2

関連ノート

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