(3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate → tert-Butyl (3S,4S)-4-amino-3-fluoropiperidine-1-carboxylate

HRID 588482Notes

Reaction equation

HRID 588482 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>CCO.[Pd]>[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 53979198(3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate

Product 1

HCID 57415840tert-Butyl (3S,4S)-4-amino-3-fluoropiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd/C 10% (4.5 g) was added to a solution of (3S,4S) tert-butyl 4-(benzyl amino)-3-fluoropiperidine-1-carboxylate, 2.9 (19.1 g, 0.062 mol) in EtOH (500 mL). The reaction was stirred under hydrogen atmosphere (balloon pressure) for 16 hours at room temperature. After completion of reaction by TLC, the mixture was filtered through celite-bed and concentrated under reduced pressure to obtain the title compound (3S,4S) tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate, 2.11 (12.6 g, 93% yield). 1HNMR (CDCl3, 400 MHz): δ 4.33-4.14 (m, 1H), 4.13-4.02 (m, 2H), 2.94-2.78 (m, 3H), 1.89-1.86 (m, 1H), 1.48 (s, 9H), 1.42-1.34 (m, 1H); LCMS: 100%, m/z 163.1 (M−55, tert-But); HPLC: 99.17%, rt=5.146 min.

Workup

  1. customAfter completion of reaction by TLC
  2. filtrationthe mixture was filtered through celite-bed and
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36e39c1eb84241539525e50b2b1d8046
Source dataset
uspto-grants-2016_01
Patent number
US09227969B2

Reaction notes

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