HCID 10852331, compound → rac-tert-butyl (3R,4R)-4-amino-3-fluoropiperidine-1-carboxylate

HRID 588483Notes

Reaction equation

HRID 588483 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 10852331HCID 10852331, compound

Product 1

HCID 45489895rac-tert-butyl (3R,4R)-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 (3R,4R) tert-butyl 4-(benzyl amino)-3-fluoropiperidine-1-carboxylate, 2.10 (19.6 g, 0.063 mol) in EtOH (500 mL). The reaction was stirred under hydrogen atmosphere (balloon pressure) for 16 hour. After completion of reaction by TLC, the mixture was filtered through celite-bed and concentrated under reduced pressure to obtain the title compound (3R,4R) tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate, 2.12 (12.6 g, 92% 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: 99.62%, rt=5.214 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-4986488beccb4e9ea17b88f3b1db34b2
Source dataset
uspto-grants-2016_01
Patent number
US09227969B2

Reaction notes

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