Methyl (3S,4R)-4-(benzylamino)-3-methylpiperidine-1-carboxylate → Methyl (3S,4R)-4-amino-3-methylpiperidine-1-carboxylate

HRID 655770Notes

Reaction equation

HRID 655770 reaction equation
C([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][C@@H:10]1[CH3:19])C1C=CC=CC=1>CO.[H][H].[Pd]>[NH2:8][C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][C@@H:10]1[CH3:19]

Participants

5

Reactant 1

HCID 58075022Methyl (3S,4R)-4-(benzylamino)-3-methylpiperidine-1-carboxylate

Product 1

HCID 58075083Methyl (3S,4R)-4-amino-3-methylpiperidine-1-carboxylateYield 101.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Methyl (3S,4R)-4-(benzylamino)-3-methylpiperidine-1-carboxylate (8.0 g, 0.02 mol) was dissolved in methanol (200 mL) and hydrogenated at room temperature, under 50 psi of hydrogen pressure, in the presence of palladium (2.5 g) on carbon for 2 h. The solution was then filtered and concentrated under reduced pressure to yield 3.5 g (92%) Methyl (3S,4R)-4-amino-3-methylpiperidine-1-carboxylate as liquid.

Workup

  1. filtrationThe solution was then filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e25b30d485d84329aefc171162f2844d
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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