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

HRID 222448

Reaction equation

HRID 222448 reaction equation
[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]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 13771167(R)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-oneYield 107.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a03349e921f9436080d515cb9d94a4c2
Source dataset
uspto-grants-2012_06
Patent number
US08207223B2

Linked notes

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