Sodium Cyanide → 4-[3-(1-Methoxyimino-indan-5-yl)-4-oxo-4-pyridin-4-yl-butanoyl]-piperidine-1-carboxylic acid benzyl ester

HRID 271523Notes

Reaction equation

HRID 271523 reaction equation
[C-]#N.[Na+].[N:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][CH:5]=1.[CH2:12]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28](=[O:43])/[CH:29]=[CH:30]/[C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[C:36](=[N:40][O:41][CH3:42])[CH2:35][CH2:34]3)[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[CH2:12]([O:19][C:20]([N:22]1[CH2:23][CH2:24][CH:25]([C:28](=[O:43])[CH2:29][CH:30]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[C:36](=[N:40][O:41][CH3:42])[CH2:35][CH2:34]3)[C:10](=[O:11])[C:7]2[CH:8]=[CH:9][N:4]=[CH:5][CH:6]=2)[CH2:26][CH2:27]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 133894-PyridinecarboxaldehydeHCID 866001274-[(E)-3-(1-Methoxyimino-indan-5-yl)-allanoyl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 866001284-[3-(1-Methoxyimino-indan-5-yl)-4-oxo-4-pyridin-4-yl-butanoyl]-piperidine-1-carboxylic acid benzyl esterYield 65%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of sodium cyanide (240 mg, 4.8 mmol) in DMF (15 ml) was treated with a solution of pyridine-4-carbaldehyde (1.71 g, 16 mmol) in DMF (25 ml). After 15 minutes a solution of the product of Step 2 (6.92 g, 16 mmol) in DMF (20 ml) was added dropwise. After stirring at room temperature for 18 hours the mixture was diluted with saturated sodium bicarbonate solution and ethyl acetate. 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 (5.6 g, 65%); MS(ES+) m/e 540 [M+H]+.

Workup

  1. washThe organic phase was washed with water and brine
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-92abf0462dfe4f579fbb5a9c4d59ca17
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

Loading…