Sodium borohydride → HCID 70235707, compound

HRID 1384303Notes

Reaction equation

HRID 1384303 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:22](=[O:39])[CH:23]([N:25]2[CH2:30][CH2:29][C:28]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)([OH:31])[CH2:27][CH2:26]2)[CH3:24])[CH:7]=[C:8]([F:21])[C:9]=1[O:10][Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13]>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([C@@H:22]([OH:39])[C@H:23]([N:25]2[CH2:26][CH2:27][C:28]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)([OH:31])[CH2:29][CH2:30]2)[CH3:24])[CH:7]=[C:8]([F:21])[C:9]=1[O:10][Si:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186595HCID 21186595, compound

Product 1

HCID 70235707HCID 70235707, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.058 g, 1.40 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(3,5-difluoro-4-triisopropylsilyloxyphenyl)-2-(4-(-4-chlorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (0.76 g, 1.38 mmol in 20 mL of ethanol) was added. The reaction was stirred at ambient temperature over the weekend. The white solid which precipitated was collected by filtration and dried to yield 0.43 g (57%) of (1R*,2R*)-1-(3,5-difluoro-4-triisopropylsilyloxyphenyl)-2-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-ol which was suitable for use without further purification and had: mp 192-192.5° C. Analysis calculated for C29H42ClF2NO3Si.0.25 H2O: C, 62.35; H, 7.67; N, 2.51. Found: C, 62.37; H, 7.81; N, 2.73.

Workup

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

Sources & evidence

ORD record
ord-004047694c3c4adfa7ac825ae32f0fe4
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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