Sodium Methoxide → 4-[(E)-3-(1-Methoxyimino-indan-5-yl)-allanoyl]-piperidine-1-carboxylic acid benzyl ester

HRID 271522Notes

Reaction equation

HRID 271522 reaction equation
N1CCC(C2OC(C3C=CN=CC=3)=[C:9]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[C:23](=[N:27][OH:28])[CH2:22][CH2:21]4)C=2)CC1.[CH3:29][O-].[Na+].[CH2:32]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH:45]([C:48](=[O:50])[CH3:49])[CH2:44][CH2:43]1)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CO>[CH2:32]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH:45]([C:48](=[O:50])/[CH:49]=[CH:9]/[C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[C:23](=[N:27][O:28][CH3:29])[CH2:22][CH2:21]3)[CH2:44][CH2:43]1)=[O:41])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 19065050Benzyl 4-acetylpiperidine-1-carboxylateHCID 1363419135-(5-Piperidin-4-yl-2-pyridin-4-yl-furan-3-yl)-indan-1-one oxime

Product 1

HCID 866001274-[(E)-3-(1-Methoxyimino-indan-5-yl)-allanoyl]-piperidine-1-carboxylic acid benzyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product of Step 1 (4.8 g, 25 mmol), sodium methoxide (1.35 g, 25 mmol) and 4-acetyl-piperidine-1-carboxylic acid benzyl ester (6.4 g, 25 mmol) (WO97/05877) in methanol (100 ml) was heated at reflux for 8 hours. After cooling to room temperature the solution was concentrated in vacuo and the residue diluted with ethyl acetate and water. The organic phase was washed with water and brine, dried and concentrated in vacuo and the residue purified by silica gel chromatography to give the title compound (6.92 g, 64%); MS(ES+) m/e 433 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. concentrationwas concentrated in vacuo
  4. additionthe residue diluted with ethyl acetate and water
  5. washThe organic phase was washed with water and brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-4781bada4b6243bfbe4cdb0ddf1e891b
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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