(+/-)-cis-4-Azidomethyl-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester → tert-butyl (3S,4R)-4-(aminomethyl)-3-fluoropiperidine-1-carboxylate

HRID 402075Notes

Reaction equation

HRID 402075 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][N:15]=[N+]=[N-])[C@H:10]([F:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][NH2:15])[C@H:10]([F:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86657835(+/-)-cis-4-Azidomethyl-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86657837tert-butyl (3S,4R)-4-(aminomethyl)-3-fluoropiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (±)-cis-4-azidomethyl-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester (0.68 mmol, 160 mg) in methanol (1.5 mL) was added Pd—C (20% by wt., 35 mg). The reaction was hydrogenated under balloon pressure for 2 h at room temperature. The reaction was filtered through a bed of celite. The solvent was evaporated to provide (±)-cis-4-aminomethyl-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. filtrationThe reaction was filtered through a bed of celite
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8232a758eb144d3cbff3d564b46df2fd
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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