Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 54265678, compound

HRID 975635Notes

Reaction equation

HRID 975635 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C@H:8]1[CH:20]=O)=[O:6])[CH:2]=[CH2:3].C1(P(=[CH:41][C:42]([O:44][CH3:45])=[O:43])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15])[CH2:9][C@H:8]1[CH:20]=[CH:41][C:42]([O:44][CH3:45])=[O:43])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 22870383(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidine

Product 1

HCID 54265678HCID 54265678, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidine (30.0 g) in tetrahydrofuran (300 ml) was added methyl (triphenylphosphoranylidene)acetate (35.2 g) and the mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was chromatographed on a 300 g of silica gel to give (2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(3-methoxy-3-oxo-1-propenyl)pyrrolidine (29.8 g) as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed on a 300 g of silica gel

Sources & evidence

ORD record
ord-e34948c905884a10b473d49a8a73f3d6
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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