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

HRID 1425135Notes

Reaction equation

HRID 1425135 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][CH:24]=[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][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86648602tert-Butyl cis(+/-)-4-(benzylamino)-3-allyloxypiperidine-1-carboxylate

Product 1

HCID 67548306Tert-butyl cis(+/-)-4-amino-3-propoxypiperidine-1-carboxylateYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The same operation as in Example (90d) was performed using tert-butyl cis(±)-4-(benzylamino)-3-allyloxypiperidine-1-carboxylate obtained in Example (113c) (4.96 g, 14.3 mmol), 10% Pd/C (wet, 1.5 g), ammonium formate (5.42 g, 86 mmol) and methanol (30 mL), to obtain 3.41 g of the title compound as a colorless oily substance (93%).

Sources & evidence

ORD record
ord-578f4cff83324f08bfee403836b0fe2f
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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