Nitrogen → tert-Butyl 4-amino-3,3-difluoropiperidine-1-carboxylate

HRID 2280375Notes

Reaction equation

HRID 2280375 reaction equation
N#N.C([NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C:12]1([F:25])[F:24])C1C=CC=CC=1>CO.[Pd]>[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][C:12]1([F:25])[F:24]

Participants

5

Reactant 2

HCID 947NitrogenHCID 66710726tert-Butyl 4-(benzylamino)-3,3-difluoropiperidine-1-carboxylate

Product 1

HCID 56932105tert-Butyl 4-amino-3,3-difluoropiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), tert-butyl 4-(benzylamino)-3,3-difluoropiperidine-1-carboxylate (0.186 g, 0.57 mmol) was dissolved in MeOH (5 mL) and wet Pd/C 10% (50 mg) was added. The flask was purged with H2 gas and the reaction mixture stirred under an H2 atmosphere for 2 h at rt. The reaction mixture was filtered over celite and the cake was washed with MeOH and EA. The filtrate was concentrated under reduced pressure to give tert-butyl 4-amino-3,3-difluoropiperidine-1-carboxylate as a colorless oil. LC-MS-conditions 08: tR=0.49 min; [M-CH3+H]+=222.32.

Workup

  1. customThe flask was purged with H2 gas
  2. filtrationThe reaction mixture was filtered over celite
  3. washthe cake was washed with MeOH and EA
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2aac53795fe049d684178aa48c838a19
Source dataset
uspto-grants-2015_09
Patent number
US09139524B2

Reaction notes

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