Tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate → 1,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylate

HRID 339704Notes

Reaction equation

HRID 339704 reaction equation
C([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]1[F:22])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CCO>[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 21948938Tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate

Product 1

HCID 112644351,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylateYield 97.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a 250 mL glass Parr vessel was added the product from Step C (14.8 g, 48.0 mmol) and EtOH (100 mL). Pearlman's Catalyst (4.72 g, 3.36 mmol) was added and the mixture was shaken in a Parr reactor under 40-45 psi H2 for 15 hours. The reaction was filtered through celite and the celite was washed with EtOAc. The filtrate was concentrated and the residue was dissolved in CH2Cl2 and filtered through celite, and the celite was washed with CH2Cl2 and EtOAc. The filtrate was concentrated to afford 10.2 g (92%) of the desired product as a thick oil that slowly solidified to a white solid.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washthe celite was washed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in CH2Cl2
  5. filtrationfiltered through celite
  6. washthe celite was washed with CH2Cl2 and EtOAc
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-af232c0af60544f6835140272ae9d548
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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