Ammonium formate → rac-tert-butyl (3R,4R)-4-amino-3-fluoropiperidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14]CC2C=CC=CC=2)[C@H:10]([F:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH2:14])[C@H:10]([F:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A stirred solution of trans-4-benzylamino-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester (0.170 g, 0.551 mmol) in methanol (2 ml) and was treated with ammonium formate (0.139 g, 2.20 mmol) and 10% palladium on activated carbon (0.059 g, 0.055 mmol) and stirred at 50° C. for one hour. The mixture was then filtered through Celite, washed with copious methanol and concentrated under vacuum to give 118 mg (100%) of trans-4-amino-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester that was used without further purification. LCMS (Method F): RT=0.14 min, m+H=219.0; 1H NMR (400 MHz, DMSO) δ 4.22-4.01 (m, 1H), 3.96-3.68 (m, 2H), 3.62-3.52 (m, 1H), 3.22-2.94 (m, 2H), 2.89-2.77 (m, 1H), 1.81-1.63 (m, 2H), 1.39 (s, 10H), 1.28-1.16 (m, 1H).
Workup
- filtrationThe mixture was then filtered through Celite
- washwashed with copious methanol
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-ea21a7cd9c1c41609f91fe4bcf00557f
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461328B2
Reaction notes
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