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

HRID 1425443Notes

Reaction equation

HRID 1425443 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-eb7372730d4a443caab96dc621c3ffd7
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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