Ethyl cis(+/-)-3-(4-{benzyl[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylbenzoate → Ammonium formate

HRID 43973Notes

Reaction equation

HRID 43973 reaction equation
C([N:8](C(OCC1C=CC=CC=1)=O)[C@H:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[C:17]([CH:23]=[C:24]([CH3:26])[CH:25]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11][C@H:10]1[O:27][CH3:28])C1C=CC=CC=1>[C].[Pd].C(O)C>[CH:18]([O-:20])=[O:19].[NH4+:8].[NH2:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[C:17]([CH:23]=[C:24]([CH3:26])[CH:25]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11][C@H:10]1[O:27][CH3:28]

Participants

5

Reactant 1

HCID 86648853Ethyl cis(+/-)-3-(4-{benzyl[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylbenzoate

Product 2

HCID 2723923Ammonium formateYield 2,000%HCID 86648852Ethyl 3-[(3R,4S)-4-amino-3-methoxypiperidin-1-yl]-5-methylbenzoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

The same operation as in Example (90d) was performed using ethyl cis(±)-3-(4-{benzyl[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methylbenzoate obtained in Example (259f) (126 mg, 0.24 mmol), a 10% palladium-carbon catalyst (63 mg), ammonium formate (155 mg, 2.4 mmol) and ethanol (5 mL), to obtain the title compound. The resulting compound was used for the next reaction without purification.

Sources & evidence

ORD record
ord-34942812aaf54d8e82525a005a543fbc
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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