HCID 46191161, compound → HCID 46224954, compound

HRID 451904Notes

Reaction equation

HRID 451904 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:36])[NH:24][C@H:25]([CH2:33][NH:34][CH3:35])[CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[CH:27]1([CH2:26][C@H:25]([NH:24][C:23]([N:19]2[CH2:20][CH2:21][CH2:22][C@@H:17]([C@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=3)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH2:18]2)=[O:36])[CH2:33][NH:34][CH3:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 1

HCID 46191161HCID 46191161, compound

Product 1

HCID 46224954HCID 46224954, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of fumarate salt (0.120 g) of methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-cyclohexyl-3-(methylamino)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate, HCO2NH4 (1.200 g), and 10% Pd/C (0.150 g) in MeOH was stirred at rt for 3 d. The mixture was filtered off precipitates through Celite® 545 and washed with MeOH. After the solvent was evaporated under reduced pressure, the crude methyl 2-((R)—((R)-1-((S)-1-cyclohexyl-3-(methylamino)propan-2-ylcarbamoyl)piperidin-3-yl)(phenyl)methoxy)ethylcarbamate was directly used in the next step without further purification. MS ESI +ve m/z 489 (M+H).

Workup

  1. filtrationThe mixture was filtered off
  2. customprecipitates through Celite® 545
  3. washwashed with MeOH
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe crude methyl 2-((R)—((R)-1-((S)-1-cyclohexyl-3-(methylamino)propan-2-ylcarbamoyl)piperidin-3-yl)(phenyl)methoxy)ethylcarbamate was directly used in the next step without further purification

Sources & evidence

ORD record
ord-b96855248d764ba4be9ad460529bad4c
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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