Ammonium formate → tert-Butyl cis(+/-)-4-amino-3-(2,2-difluoropropoxy)piperidine-1-carboxylate

HRID 43712Notes

Reaction equation

HRID 43712 reaction equation
C([N:8](C(OCC1C=CC=CC=1)=O)[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][C:24]([F:27])([F:26])[CH3:25])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][C:24]([F:27])([F:26])[CH3:25]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86648657tert-Butyl cis(+/-)-4-{benzyl[(benzyloxy)carbonyl]amino}-3-(2,2-difluoropropoxy)piperidine-1-carboxylate

Product 1

HCID 86648656tert-Butyl cis(+/-)-4-amino-3-(2,2-difluoropropoxy)piperidine-1-carboxylateYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The same operation as in Example (90d) was performed using tert-butyl cis(±)-4-{benzyl[(benzyloxy)carbonyl]amino}-3-(2,2-difluoropropoxy)piperidine-1-carboxylate obtained in Example (128c) (1.31 g, 2.5 mmol), 10% Pd/C (wet, 0.4 g), ammonium formate (0.95 g, 15 mmol) and methanol (20 mL), to obtain 0.69 g of the title compound as a colorless oily substance (64%).

Sources & evidence

ORD record
ord-0938eb97bbe545139357a9812cde5ea2
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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