Triethylamine → (S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one

HRID 1710122Notes

Reaction equation

HRID 1710122 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].C(N(CC)CC)C>ClCCl>[CH3:12][C:11]([Si:8]([CH3:10])([CH3:9])[O:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11029774(3S)-3-hydroxypyrrolidin-2-one

Product 1

HCID 10584804(S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-oneYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 14 g of (S)-3-hydroxy-2-pyrrolidinone, 45 g of tert-butyldimethylsilyl chloride, 50 ml of triethylamine and 500 ml of dichloromethane was stirred overnight. The solution was washed four times with water, once with brine, dried and concentrated in vacuo. The residue was dissolved in 500 ml of methanol, refluxed overnight and concentrated in vacuo. The residue was purified by chromatography (silica gel), giving 21.5 g of (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pyrrolidinone; [α]D26° =-52° (dichloromethane); mp 48°-49° C.

Workup

  1. washThe solution was washed four times with water
  2. dry with materialonce with brine, dried
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in 500 ml of methanol
  5. temperaturerefluxed overnight
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-31a6386a38b241fb8a12829b374cf699
Source dataset
uspto-grants-1990_08
Patent number
US04952600

Reaction notes

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