tert-butyl (3R)-3-formylpyrrolidine-1-carboxylate → (S)-tert-Butyl 3-vinylpyrrolidine-1-carboxylate

HRID 1026175Notes

Reaction equation

HRID 1026175 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@@H:20]([CH:23]=O)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@@H:20]([CH:23]=[CH2:1])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 1514342tert-butyl (3R)-3-formylpyrrolidine-1-carboxylateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 66975072(S)-tert-Butyl 3-vinylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of methyltriphenylphosphonium bromide (450 g, 1.3 mmol, 3.0 eq.) in THF (200 mL) was cooled to −78° C. 2M Sodium bis(trimethylsilyl)amide (580 mL, 2.8 eq.) was added and the mixture was stirred for 3 hours. A solution of (R)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester (84 g, 421.6 mmol, 1.0 eq.) in THF (100 mL) was added dropwise at −65°. Upon completion of the reaction, the product was purified by column chromatography (200-300 mesh, hexanes:EtOAc=1:3, 3 L) to yield (S)-3-vinyl-pyrrolidine-1-carboxylic acid t-butyl ester (40 g).

Workup

  1. customUpon completion of the reaction
  2. customthe product was purified by column chromatography (200-300 mesh, hexanes:EtOAc=1:3, 3 L)

Sources & evidence

ORD record
ord-1194e2b34b0e4d79a9742a68d36dbc0e
Source dataset
uspto-grants-2014_05
Patent number
US08729119B2

Reaction notes

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