Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Benzyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate

HRID 1664768Notes

Reaction equation

HRID 1664768 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:37][C:38]([O:40][CH3:41])=[O:39])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH3:41][O:40][C:38](=[O:39])[CH:37]=[C:14]1[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 57362584Benzyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylateYield 60.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of N-benzyloxycarbonyl-4-piperidinone (5.0 g, 21.4 mol) and methyl (triphenylphosphoranylidene)acetate (10.0 g, 30.0 mmol) in benzene (100 mL) was heated at 75° C. for 48 h. The reaction was concentrated, diluted with ether, the precipitate filtered off, and the rinsate concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 20 to 60% ethyl acetate:hexanes to give the title compound (5.25 g). MS: m/z=290.1 (M+1).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ether
  3. filtrationthe precipitate filtered off
  4. concentrationthe rinsate concentrated
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of 20 to 60% ethyl acetate

Sources & evidence

ORD record
ord-f0d54235a04047628d0e47ca553b15b1
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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