ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate → (4R,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-one

HRID 1173620Notes

Reaction equation

HRID 1173620 reaction equation
C(OC([NH:11][C@@H:12]([CH2:28][CH3:29])[CH:13]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:14][C:15](OCC)=[O:16])=O)C1C=CC=CC=1>CO.[C].[Pd]>[Si:21]([O:20][C@H:13]1[C@H:12]([CH2:28][CH3:29])[NH:11][C:15](=[O:16])[CH2:14]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].[Si:21]([O:20][C@@H:13]1[C@H:12]([CH2:28][CH3:29])[NH:11][C:15](=[O:16])[CH2:14]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

5

Reactant 1

HCID 67105077ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate

Product 2

HCID 59557019(4R,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-oneYield 59%HCID 67105254(4S,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-oneYield 13%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate (64.0 g) in methanol (500 mL) was added 10% palladium carbon (containing 50% water, 6.5 g), and the mixture was stirred at room temperature for 3.5 hr under a hydrogen atmosphere and filtered. Sodium methoxide (13.6 g) was added to the filtrate, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20/1→1/4) to give the title compound (yield: 21.6 g, 59%) and (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-one (yield: 4.64 g, 13%) as a colorless solid and a colorless oil, respectively.

Workup

  1. filtrationfiltered
  2. additionSodium methoxide (13.6 g) was added to the filtrate
  3. stirringthe mixture was stirred at room temperature for 2 hr
  4. additionWater was added to the reaction mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20/1→1/4)

Sources & evidence

ORD record
ord-75ad5d3a6cc34b98a6e3650b45272d31
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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