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

HRID 497075

Reaction equation

HRID 497075 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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%):

Workup

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

Sources & evidence

ORD record
ord-15a1ecbc71dc4a95a037f2d5cec9f155
Source dataset
uspto-grants-2005_09
Patent number
US06949553B2

Linked notes

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