(3S,4R)-1-benzyl-4-trifluoromethyl-piperidine-3,4-diol → (3S,4R)-4-trifluoromethyl-piperidine-3,4-diol

HRID 734771Notes

Reaction equation

HRID 734771 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@:11]([C:15]([F:18])([F:17])[F:16])([OH:14])[C@@H:10]([OH:19])[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[F:18][C:15]([F:16])([F:17])[C@@:11]1([OH:14])[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[OH:19]

Participants

5

Reactant 2

HCID 69056096(3S,4R)-1-benzyl-4-trifluoromethyl-piperidine-3,4-diolHCID 178418361HCID 178418361, compound

Product 1

HCID 57845299(3S,4R)-4-trifluoromethyl-piperidine-3,4-diol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.50 g (5.45 mmol) of (3S,4R)-1-benzyl-4-trifluoromethylpiperidin-3,4-diol and 170 mg of Pd/C (10%) in 17 mL of MeOH was hydrogenated at RT and 3 bar hydrogen pressure for 5 hours. The catalyst was filtered off and the filtrate was evaporated down in vacuo. Yield: 910 mg (90% of theoretical); C6H10F3NO2 (M=185.144); calc.: molpeak (M+H)+: 186; found: molpeak (M+H)+: 186; Rf value: 0.35 (silica gel, EtOAc/MeOH/conc. aqueous ammonia 7:3:0.3).

Workup

  1. customwas hydrogenated at RT
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated down in vacuo

Sources & evidence

ORD record
ord-90eac971f1af47f58df0a523783866df
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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