Butyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylate → Butyl cis(+/-)-2-(4-amino-3-ethoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylate

HRID 43669Notes

Reaction equation

HRID 43669 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[O:19][C:20]([CH2:30][CH3:31])=[C:21]([C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[N:22]=2)[CH2:14][C@H:13]1[O:32][CH2:33][CH3:34])=O)C1C=CC=CC=1>[Pd].CO>[NH2:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[O:19][C:20]([CH2:30][CH3:31])=[C:21]([C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[N:22]=2)[CH2:14][C@H:13]1[O:32][CH2:33][CH3:34]

Participants

4

Reactant 1

HCID 86648613Butyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylate

Product 1

HCID 86648612Butyl cis(+/-)-2-(4-amino-3-ethoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylateYield 104.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The same operation as in Example (95b) was performed using butyl cis(±)-2-(4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylate obtained in Example (115a) (1.21 g, 2.5 mmol), 10% Pd/C (0.25 g) and methanol (15 mL), to obtain 0.89 g of the title compound as a light brown oily substance (97%).

Sources & evidence

ORD record
ord-1230134fae3f4ef0ae4e0dc06e8a2bbd
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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