HCID 57554870, compound → HCID 57554647, compound

HRID 1511867Notes

Reaction equation

HRID 1511867 reaction equation
C(OC([NH:11][C@:12]1([C:34]([O:36][CH3:37])=[O:35])[CH2:16][CH2:15][C@@H:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)=[CH:19][CH:18]=2)[CH2:13]1)=O)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[NH2:11][C@:12]1([C:34]([O:36][CH3:37])=[O:35])[CH2:16][CH2:15][C@@H:14]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)=[CH:21][CH:22]=2)[CH2:13]1

Participants

4

Reactant 1

HCID 57554870HCID 57554870, compound

Product 1

HCID 57554647HCID 57554647, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent2×

Procedure

A solution of (1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-(2-(3-methoxyphenoxy)ethyl)phenyl)cyclopentanecarboxylate (0.266 g, 0.528 mmol) in EtOH (2.0 ml) was added to a slurry of Pearlman's Catalyst (0.019 g, 0.026 mmol) in EtOH (5.28 ml). Hydrogen gas was then bubbled through the reaction mixture for 2-3 minutes. The resulting mixture was stirred under the atmosphere of hydrogen overnight. The crude mixture was filtered through Celite® and the filtrate was concentrated in vacuo to yield (1R,3R)-methyl 1-amino-3-(4-(2-(3-methoxyphenoxy)ethyl) phenyl)cyclopentanecarboxylate (157 mg, 0.425 mmol) as colorless oil.

Workup

  1. customHydrogen gas was then bubbled through the reaction mixture for 2-3 minutes
  2. filtrationThe crude mixture was filtered through Celite®
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3245753ff1bc4fcb98fd98106f6c109b
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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