Sodium borohydride → HCID 70236000, compound

HRID 1384305Notes

Reaction equation

HRID 1384305 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]([CH:18]([OH:38])[CH: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 70236000HCID 70236000, compound

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-trifluoromethylphenyl)-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-d0941274d14045e8aef7697c091232b4
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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