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

HRID 43680Notes

Reaction equation

HRID 43680 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][C:24]([CH3:26])=[CH2:25])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][CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86648620tert-Butyl cis(+/-)-4-(benzylamino)-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylate

Product 1

HCID 86648621tert-Butyl cis(+/-)-4-amino-3-isobutoxypiperidine-1-carboxylateYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The same operation as in Example (90d) was performed using tert-butyl cis(±)-4-(benzylamino)-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylate obtained in Example (117c) (1.8 g, 5 mmol), 10% Pd/C (wet, 0.5 g), ammonium formate (2.52 g, 40 mmol) and methanol (20 mL), to obtain 1.26 g of the title compound as a colorless oily substance (93%).

Sources & evidence

ORD record
ord-1d6c9d76e5a747ce849368e40161cad7
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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