cis-4-Benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine → 1,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylate

HRID 877669Notes

Reaction equation

HRID 877669 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].[H][H]>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 11312869cis-4-Benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 112644351,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylateYield 85.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (+/−)-(cis)-tert-butyl-4-(benzylamino)-3-fluoropiperidine-1-carboxylate (100 mg, 0.32 mmol) and 10% Pd/C (10 mg) in methanol (20 mL) was stirred under a balloon of hydrogen for 2 h at room temperature. The reaction mixture was purged with argon, filtered over Celite, rinsed with methanol (10 mL) and the resulting filtrate was concentrated under vacuum to give the title compound as a colorless oil (60 mg, 85%). 1H-NMR (400 MHz, CDCl3) δ ppm: 4.49-4.61 (d, J=48.4 Hz, 1H), 4.30 (s, 1H), 4.07 (s, 1H), 2.84-3.08 (m, 3H), 1.67-1.69 (m, 2H), 1.47 (s, 9H), 1.32 (s, 2H). 19F-NMR (400 MHz in CDCl3): δ ppm: −205.75-206.03 (1F).

Workup

  1. customThe reaction mixture was purged with argon
  2. filtrationfiltered over Celite
  3. washrinsed with methanol (10 mL)
  4. concentrationthe resulting filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-fa84e1dcdabf4b5bbd484032e56468fd
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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