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

HRID 43653Notes

Reaction equation

HRID 43653 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[O:19][C:20]([CH3:30])=[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:31][CH2:32][CH3:33])=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]([CH3:30])=[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:31][CH2:32][CH3:33]

Participants

4

Reactant 1

HCID 86648599Butyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-methyl-1,3-oxazole-4-carboxylate

Product 1

HCID 86648598Butyl cis(+/-)-2-(4-amino-3-ethoxypiperidin-1-yl)-5-methyl-1,3-oxazole-4-carboxylateYield 96.6%

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-methyl-1,3-oxazole-4-carboxylate obtained in Example (112g) (1.05 g, 2.1 mmol), 10% Pd/C (0.25 g) and methanol (15 mL), to obtain 0.66 g of the title compound as a light brown oily substance (88%).

Sources & evidence

ORD record
ord-7ddf58b99e7b49f3a2460b905233ad7d
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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