Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(1-Boc-2-pyrrolidinyl)acrylate

HRID 1619395Notes

Reaction equation

HRID 1619395 reaction equation
[CH:1]([CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.[C:15]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:17][CH2:18][CH3:19])=[O:16]>C1COCC1>[CH2:18]([O:17][C:15](=[O:16])[CH:20]=[CH:1][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:19]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 42278151-Boc-2-Formylpyrrolidine

Product 1

HCID 53933727Ethyl 3-(1-Boc-2-pyrrolidinyl)acrylateYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 2-formylpyrrolidine-1-carboxylate (4 g, 20 mmol) and (carbethoxymethylene)triphenylphosphorane (7 g, 20 mmol) in THF was stirred at room temperature for 2 hr. Then the mixture was concentrated and purified by column chromatography to give 4 g of desired product. MS (ESI): 270 (MH+).

Workup

  1. concentrationThen the mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-3e2b99e6f9ca419d8bc31e26ebd3c0de
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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