Sodium borohydride → HCID 54480353, compound

HRID 1003610Notes

Reaction equation

HRID 1003610 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[C:16]([F:17])=[CH:15][C:14]([C:18](=[O:38])[CH:19]([N:21]2[CH2:26][CH2:25][C:24]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)([OH:27])[CH2:23][CH2:22]2)[CH3:20])=[CH:13][C:12]=1[F:39])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([O:10][C:11]1[C:12]([F:39])=[CH:13][C:14]([C@@H:18]([OH:38])[C@H:19]([N:21]2[CH2:22][CH2:23][C:24]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([F:35])([F:37])[F:36])=[CH:32][CH:33]=3)([OH:27])[CH2:25][CH2:26]2)[CH3:20])=[CH:15][C:16]=1[F:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186659HCID 21186659, compound

Product 1

HCID 54480353HCID 54480353, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.085 g, 2.25 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(4-benzyloxy-3,5-difluorophenyl)-2-(4-(4-trifluoromethylphenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (1.02 g, 1.96 mmol in 30 mL of ethanol) was added. The reaction was stirred at ambient temperature overnight. The white solid which precipitated was collected by filtration and dried to yield 0.66 g (65%) of (1R*,2R*)-1-(4-benzyloxy-3,5-difluorophenyl)-2-(4-(4-trifluormethylphenyl)-4-hydroxypiperidin-1-yl)-propan-1-ol which was suitable for use without further purification and had: mp 201-202° C. Analysis calculated for C28H28F5NO3.0.25 H2O: C, 63.93; H, 5.46; N, 2.66. Found: C, 63.98; H, 5.49; N, 2.70.

Workup

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. customThe white solid which precipitated
  3. filtrationwas collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-374cc261f0f145ff96cbd81786fb7a3d
Source dataset
uspto-grants-2000_04
Patent number
US06046213

Reaction notes

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