Sodium borohydride → HCID 68704632, compound

HRID 1434591Notes

Reaction equation

HRID 1434591 reaction equation
[BH4-].[Na+].[CH3:3][S:4]([C:7]1[CH:31]=[CH:30][C:10]2[N:11]([CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:23])[CH2:16][CH2:15]3)[CH:12]=[N:13][C:9]=2[CH:8]=1)(=[O:6])=[O:5]>C(O)C>[CH3:3][S:4]([C:7]1[CH:31]=[CH:30][C:10]2[N:11]([CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[OH:23])[CH2:16][CH2:15]3)[CH:12]=[N:13][C:9]=2[CH:8]=1)(=[O:6])=[O:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57935976HCID 57935976, compound

Product 1

HCID 68704632HCID 68704632, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (189 mg) was added to a solution of 3-{4-[5-(methylsulfonyl)-1H-benzimidazol-1-yl]piperidin-1-yl}-1-phenylpropan-1-one (2.07 g) in ethanol (40 ml) at 0° C., the mixture was allowed to warm to room temperature and was stirred for 16 hours. The reaction mixture was evaporated to dryness, the residue was redissolved in dichloromethane and washed with water (15 ml) and brine (15 ml) and dried. Removal of the solvent gave 3-{4-[5-(methylsulfonyl)-1H-benzimidazol-1-yl]piperidin-1-yl}-1-phenylpropan-1-ol, 2.1 g, M+H 414.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue was redissolved in dichloromethane
  3. washwashed with water (15 ml) and brine (15 ml)
  4. customdried
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-3ae6950eaf34440caacf3571db161d47
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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