Ammonium formate → tert-Butyl cis(+/-)-4-amino-3-(3-fluoropropoxy)piperidine-1-carboxylate

HRID 43708Notes

Reaction equation

HRID 43708 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[O:22][CH2:23][CH2:24][CH2:25][F:26])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH2:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][C@H:10]1[O:22][CH2:23][CH2:24][CH2:25][F:26]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86648651tert-Butyl cis(+/-)-4-(benzylamino)-3-(3-fluoropropoxy)piperidine-1-carboxylate

Product 1

HCID 86648652tert-Butyl cis(+/-)-4-amino-3-(3-fluoropropoxy)piperidine-1-carboxylateYield 105.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The same operation as in Example (95d) was performed using tert-butyl cis(±)-4-(benzylamino)-3-(3-fluoropropoxy)piperidine-1-carboxylate obtained in Example (127c) (1.06 g, 2.89 mmol), 10% Pd/C (wet, 0.4 g), ammonium formate (1.09 g, 17.4 mmol) and methanol (15 mL), to obtain 0.84 g of the title compound as a colorless oily substance (100%).

Sources & evidence

ORD record
ord-a93e8e8568fd4ad5afb5d869e74908e6
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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