Ammonium formate → Tert-butyl cis(+/-)-4-amino-3-ethoxypiperidine-1-carboxylate

HRID 43650Notes

Reaction equation

HRID 43650 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][CH3:24])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][CH3:24]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86648597tert-Butyl cis(+/-)-4-(benzylamino)-3-ethoxypiperidine-1-carboxylate

Product 1

HCID 86648467Tert-butyl cis(+/-)-4-amino-3-ethoxypiperidine-1-carboxylateYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The same operation as in Example (90d) was performed using tert-butyl cis(±)-4-(benzylamino)-3-ethoxypiperidine-1-carboxylate obtained in Example (112c) (4.06 g, 12.1 mmol), 10% Pd/C (wet, 1.1 g), ammonium formate (2.87 g, 46 mmol) and methanol (30 mL), to obtain 2.28 g of the title compound as a colorless oily substance (94%).

Sources & evidence

ORD record
ord-cc414890987a4abf9952ae6799d223db
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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