Ammonium formate → 1,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylate

HRID 1948310Notes

Reaction equation

HRID 1948310 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14]CC2C=CC=CC=2)[C@H:10]([F:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[C@H:10]([F:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11312869cis-4-Benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine2×

Product 1

HCID 112644351,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Cis(±)tert-butyl-4-(benzylamino)-3-fluoropiperidine-1-carboxylate (Intermediate 82; 711 mg), ammonium formate (582 mg), and 10% Pd/C (200 mg) in MeOH (10 ml) was heated to 50° C. for 1 h. The reaction mixture was cooled to room temperature, filtered through diatomaceous earth and concentrated under reduced pressure to give the title compound (503 mg, quantitative). NMR (CDCl3): 1.40 (s, 9H), 1.88 (m, 2H), 3.01 (m, 2H), 3.55 (m, 2H), 3.77 (m, 1H), 4.66 (d, 1H).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c01f207d8c547b88b07a3c7784c0052
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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