Sodium borohydride → HCID 54013882, compound

HRID 1384307Notes

Reaction equation

HRID 1384307 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:21](=[O:41])[CH:22]([N:24]2[CH2:29][CH2:28][C:27]([C:31]3[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[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]([C@@H:21]([OH:41])[C@H:22]([N:24]2[CH2:29][CH2:28][C:27]([C:31]3[CH:36]=[CH:35][C:34]([C:37]([F:39])([F:40])[F:38])=[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:12]([CH3:14])[CH3:13])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186654HCID 21186654, compound

Product 1

HCID 54013882HCID 54013882, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of sodium borohydride (0.049 g, 1.30 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(3-fluoro-4-triisopropylsilyloxyphenyl)-2-(4-(4-trifluoromethylphenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (0.738 g, 1.30 mmol in 10 mL of ethanol) was added with a 5 mL ethanol rinse. The reaction was stirred at ambient temperature overnight. The white precipitate which formed was collected by filtration to afford 0.335 g (45%) of (1R*,2R*)-1-(3-fluoro-4-triisopropylsilyloxyphenyl)-2-(4-(4-trifluoromethylphenyl)-4-hydroxypiperidin-1-yl)-propan-1-ol which had: NMR δ7.63 (s, 4 H), 7.07 (dd, J=2, 11.5 Hz, 1 H), 6.98-6.84 (m, 2 H), 5.13 (s, 1 H), 4.20 (d, J=9.5 Hz, 1 H), 3.06 (sym m, 1 H), 2.81-2.71 (m, 1 H), 2.70-2.50 (m, 3 H), 2.15 (sym m, 2 H), 1.81 (distorted d, J=14 Hz, 2 H), 1.59 (s, 1 H), 1.33-1.19 (m, 3 H), 1.08 (d, J=7 Hz, 18 H), 0.81 (d, J=6.5 Hz, 3 H). The product also contained about 7% of the erythro diastereomer but was suitable for use without additional purification.

Workup

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

Sources & evidence

ORD record
ord-90f079473d334eb58562c5886e31889d
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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