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

HRID 81353Notes

Reaction equation

HRID 81353 reaction equation
C([NH:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C@H:10]1[F:22])C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[NH2:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:11][C@H:10]1[F:22]

Participants

4

Reactant 1

HCID 11312869cis-4-Benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine

Product 1

HCID 112644351,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl (3R,4S)-4-benzylamino-3-fluoro-piperidine-1-carboxylate (2.13 g) is suspended in THF and mixed with a spatula tip of Pd(OH)2 and hydrogenated under H2 pressure (7 bar). For working up the catalyst is filtered off and the solvent is eliminated in vacuo and the residue is used in the next step without any further purification.

Workup

  1. filtrationis filtered off
  2. customthe residue is used in the next step without any further purification

Sources & evidence

ORD record
ord-9e424758692f4b2780134b8c74b330dc
Source dataset
uspto-grants-2014_09
Patent number
US08846689B2

Reaction notes

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