Sodium borohydride → HCID 22479244, compound

HRID 2182595Notes

Reaction equation

HRID 2182595 reaction equation
[CH3:1][O:2][C:3]([CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:38]=[CH:37][C:16]([CH2:17][C:18]23[C:26](=[O:27])[N:25]([C:28]4[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=4)[C:24](=[O:36])[N:23]2[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=1)=[O:4].[BH4-].[Na+]>CCOC(C)=O.O>[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:14]=[CH:15][C:16]([CH2:17][C:18]23[C:26](=[O:27])[N:25]([C:28]4[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=4)[C:24](=[O:36])[N:23]2[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:37][CH:38]=1)=[O:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 69214809HCID 69214809, compound

Product 1

HCID 22479244HCID 22479244, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

NiCl2.6H2O (0.17 g) was added to a solution of 6-[4-[2-(2-methoxycarbonylvinyl)phenyl]benzyl]-8-(3,5-dichlorophenyl)-1,8-diazabicyclo[4.3.0]nonane-7,9-dione (0.196 g). NaBH4 (0.14 g) was added portionwise to the mixture and the mixture was stirred for 1 hour. The mixture was diluted with EtOAc and water and filtered through Celite. The organic layer was separated and washed with water, brine, dried (MgSO4), filtered, and concentrated. Purification by chromatography (Silica gel: EtOAc/hexane: 1/4, Chromatotron) afforded the titled compound (0.125 g). MS (m/z) 573 (M++Na).

Workup

  1. filtrationfiltered through Celite
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (Silica gel: EtOAc/hexane: 1/4, Chromatotron)

Sources & evidence

ORD record
ord-5f02357648ec47a8af45e47cc9b48b4c
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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