Sodium borohydride → HCID 70233702, compound

HRID 1384306Notes

Reaction equation

HRID 1384306 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:21](=[O:38])[CH:22]([N:24]2[CH2:29][CH2:28][C:27]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)([OH:30])[CH2:26][CH2:25]2)[CH3:23])[CH:7]=[CH:8][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]([CH:21]([OH:38])[CH:22]([N:24]2[CH2:25][CH2:26][C:27]([C:31]3[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=3)([OH:30])[CH2:28][CH2:29]2)[CH3:23])[CH:7]=[CH:8][C:9]=1[O:10][Si:11]([CH:12]([CH3:13])[CH3:14])([CH:15]([CH3:17])[CH3:16])[CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186653HCID 21186653, compound

Product 1

HCID 70233702HCID 70233702, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.032 g, 0.85 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(3-fluoro-4-triisopropylsilyloxyphenyl)-2-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (0.454 g, 0.850 mmol in 10 mL of ethanol) was added. The reaction was stirred at ambient temperature overnight. The white precipitate which formed was collected by filtration to afford 0.245 g (54%) of (1R*, 2R*)-1-(3-fluoro-4-triisopropylsilyloxyphenyl)-2-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-ol which had: NMR δ7.39 (ABq, Δv1-3=35.2 Hz, J=8.5 Hz, 4 H), 7.06 (dd, J=2, 11.5 Hz, 1 H), 6.96-6.82 (m, 2 H), 5.15 (s, 1 H), 4.18 (d, J=9.5 Hz, 1 H), 3.04 (dt, J=2.5, 11.5 Hz, 1 H), 2.78-2.67 (m, 1 H), 2.67-2.52 (m, 3 H), 2.12 (sym m, 2 H), 1.80 (distorted d, J=14 Hz, 2 H), 1.54 (s, 1 H), 1.36-1.19 (m, 3 H), 1.08 (d, J=7 Hz, 18 H), 0.80 (d, J=6.5 Hz, 3 H). The product also contained about 8% of the erythro diastereomer but was suitable for use without additional purification.

Workup

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. customThe white precipitate which formed
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-8b3902fc6a9543dfa138b433e0fb810b
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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