Ammonium formate → (4-Methylpiperidin-4-yl)methanol

HRID 60286Notes

Reaction equation

HRID 60286 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][OH:16])([CH3:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].[H][H]>CO.[Pd]>[CH3:14][C:11]1([CH2:15][OH:16])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 59433298HCID 59433298, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22507737(4-Methylpiperidin-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (1-benzyl-4-methylpiperidin-4-yl)methanol (2.7 g, 12 mmol) in methanol (34 mL) was added ammonium formate (8.6 g, 135 mmol) followed by palladium on carbon (10% w/w, 3.6 g, 1.7 mmol). The reaction mixture was stirred for 18 hours under a balloon of hydrogen, then degassed, flushed with nitrogen, and filtered over a pad of celite. The solvent was removed in vacuo and the resulting residue was purified by flash chromatography (silica, 40 g, ISCO, 0-20% methanol in methylene chloride) to afford the title compound as a colorless oil, which was used in the next step without any further purification (1.2 g, 76%).

Workup

  1. customdegassed
  2. customflushed with nitrogen
  3. filtrationfiltered over a pad of celite
  4. customThe solvent was removed in vacuo
  5. customthe resulting residue was purified by flash chromatography (silica, 40 g, ISCO, 0-20% methanol in methylene chloride)

Sources & evidence

ORD record
ord-5aaf87b4066f4617860401e9e3cf779b
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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