Sodium borohydride → HCID 76587445, compound

HRID 889746Notes

Reaction equation

HRID 889746 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH:12]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=3)[CH3:11])[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 576660204-Methyl-2-(5-piperidin-3-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 76587445HCID 76587445, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

To compound 33b, 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (75 mg, 0.17 mmol), was added 4-Trifluoromethylacetophenonne (34 mg, 0.18 mmol), and titanium isopropoxide (76 mg), 0.27 mmol) under argon at room temperature. After 3 hours, add methanol ((0.76 ml), followed by sodium borohydride (10 mg, 0.27 mmol). After 5 minutes, the reaction was quenched with 0.1 N NaOH, filtered through celite and washed with dichloromethane. The solution was concentrated in vacuo, then diluted with dichloromethane, and washed with NaHCO3, and brine, and dried over magnesium sulfate. The reaction was concentrated in vacuo, and purified by silica gel chromatography to give two diastereomeric mixtures (S* and R*, tentative assignments); Calcd for C35H39F6NO2 (M+H) 619.68, Found 520.4

Workup

  1. waitAfter 5 minutes
  2. customthe reaction was quenched with 0.1 N NaOH
  3. filtrationfiltered through celite
  4. washwashed with dichloromethane
  5. concentrationThe solution was concentrated in vacuo
  6. additiondiluted with dichloromethane
  7. washwashed with NaHCO3, and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationThe reaction was concentrated in vacuo
  10. custompurified by silica gel chromatography
  11. customto give two diastereomeric mixtures (S* and R*, tentative assignments)

Sources & evidence

ORD record
ord-304837bdeac7490cb8c7eb22d6545501
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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