Hydrogen Peroxide → 4-Phenyl-4-[[1-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxyethoxy]methyl]piperidine-1-carboxylic acid tert-butyl ester

HRID 962470Notes

Reaction equation

HRID 962470 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([CH2:14][O:15][C:16]([C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=2)=[CH2:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:38].[Na+].OO>O1CCCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([CH2:14][O:15][CH:16]([C:18]2[CH:19]=[C:20]([C:28]([F:31])([F:29])[F:30])[CH:21]=[C:22]([C:24]([F:26])([F:25])[F:27])[CH:23]=2)[CH2:17][OH:38])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 537945731-tert-Butoxycarbonyl-4-phenyl-4-[1-(3,5-bis(trifluoromethyl)phenyl) vinyloxymethyl]piperidine

Product 1

HCID 105546134-Phenyl-4-[[1-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxyethoxy]methyl]piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The compound of step (c) above was treated with BH3.tetrahydrofuran (5 ml of a 1M solution in tetrahydrofuran) under an atmosphere of nitrogen for 2 hours. A mixture of 4N NaOH (10 ml) and H2O2 (5 ml of a 29% solution in water) was added and the reaction stirred for 3 hours, then extracted with diethyl ether. The ethereal extracts were washed with sodium bisulphite solution then dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether (3:7) to give the title compound as a colourless oil.

Workup

  1. additionwas added
  2. extractionextracted with diethyl ether
  3. washThe ethereal extracts were washed with sodium bisulphite solution
  4. dry with materialthen dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether (3:7)

Sources & evidence

ORD record
ord-23ad9825e3a9412e9dedb3f1660a32e7
Source dataset
uspto-grants-1998_06
Patent number
US05760018

Reaction notes

Loading…