Sodium borohydride → HCID 70233697, compound

HRID 1384302Notes

Reaction equation

HRID 1384302 reaction equation
[BH4-].[Na+].[CH3:3][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]([F:38])=[CH:34][CH:33]=3)([OH:31])[CH2:27][CH2:26]2)[CH3:24])[CH:7]=[C:8]([CH3:21])[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>[CH3:3][C:4]1[CH:5]=[C:6]([C@@H:22]([OH:39])[C@H:23]([N:25]2[CH2:30][CH2:29][C:28]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)([OH:31])[CH2:27][CH2:26]2)[CH3:24])[CH:7]=[C:8]([CH3:21])[C:9]=1[O:10][Si:11]([CH:15]([CH3:16])[CH3:17])([CH:12]([CH3:13])[CH3:14])[CH:18]([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186642HCID 21186642, compound

Product 1

HCID 70233697HCID 70233697, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.065 g, 1.72 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(3,5-dimethyl-4-triisopropylsilyloxyphenyl)-2-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (0.90 g, 1.71 mmol in 25 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 0.365 g (40%) of (1R*,2R*)-1-(3,5-dimethyl-4-triisopropylsilyloxyphenyl)-2-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-ol which was suitable for use without further purification and had: mp 186.5-187° C. Analysis calculated for C31H48FNO3Si.0.125 H2O: C, 69.69; H, 9.15; N, 2.62. Found: C, 69.65; H, 9.29; N, 2.57.

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-7cc6a6899c594d2aa5742dbc9808fab0
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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