Water → Methyl [(2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-1-pyrrolidinyl]acetate

HRID 1888321Notes

Reaction equation

HRID 1888321 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[NH:14][C:13](=[O:15])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25].O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C:13](=[O:15])[N:14]1[CH2:23][C:24]([O:26][CH3:27])=[O:25])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 60984Methyl bromoacetateHCID 13771167(R)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 56834436Methyl [(2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-1-pyrrolidinyl]acetateYield 97.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-pyrrolidinone (11.2 g) in tetrahydrofuran (97 mL) were potassium tert-butoxide (6.27 g) and methyl bromoacetate (8.11 g) at 0° C. and the solution was stirred for 2 Hours. To the reaction solution were added water, ethyl acetate and hexane and the reaction solution was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated to give the title compound (14.3 g) having the following physical data.

Workup

  1. customat 0° C.
  2. customthe reaction solution was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4fb28c6b5c2c4b6aa33fb9069292367f
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

Loading…