Sodium borohydride → HCID 54013882, compound

HRID 1003611Notes

Reaction equation

HRID 1003611 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 δ 7.63 (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-c3652460fe284e878301a0e21ae2080d
Source dataset
uspto-grants-2000_04
Patent number
US06046213

Reaction notes

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