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

HRID 1664797Notes

Reaction equation

HRID 1664797 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O=[C:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:28][CH2:27]1>C1C=CC=CC=1>[CH3:24][O:23][C:21](=[O:22])[CH:20]=[C:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:28][CH2:27]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 84.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
75 °C

Procedure

Methyl (triphenylphosphoranylidene)acetate (10.0 g, 30.0 mmol) was added to a solution of benzyl 4-oxopiperidine-1-carboxylate (5.0 g, 21.4 mmol) in benzene (100 mL) at 0° C. After 1 h, the reaction mixture was heated to 75° C. After 48 h, the mixture was concentrated and ether was added. The precipitated solid was filtered off and the filtrate was concentrated. Purification by silica gel chromatography [80% hexanes/ethyl acetate→40% hexanes/ethyl acetate)] gave the title compound (5.25 g). MS 290.1 (M+1).

Workup

  1. waitAfter 48 h
  2. concentrationthe mixture was concentrated
  3. additionether was added
  4. filtrationThe precipitated solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. customPurification by silica gel chromatography [80% hexanes/ethyl acetate→40% hexanes/ethyl acetate)]

Sources & evidence

ORD record
ord-43a565c7ad1947e6ac58a1c2cbc74716
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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