HCID 70199476, compound → HCID 70202692, compound

HRID 1276513Notes

Reaction equation

HRID 1276513 reaction equation
[C:1]1([C@@H:7]2[CH:12]=[CH:11][CH2:10][CH2:9][C@@H:8]2[C:13]([N:15]2[CH2:19][CH:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]([CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:29][CH2:28]3)[CH2:16]2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([C@@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]2[C:13]([N:15]2[CH2:19][CH:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:17]([CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:29][CH2:28]3)[CH2:16]2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 70199476HCID 70199476, compound

Product 1

HCID 70202692HCID 70202692, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 14 mg (0.03 mmol) of 1-(2(R) phenylcyclohex-3-ene-1(S)-carbonyl)-3-(RS)-((4-phenyl)piperidin-1-yl)methyl 4-(SR)-phenylpyrrolidine (from Example 182, Step B) in 2 mL of MeOH was added 10% Pd/C (7.0 mg). The reaction mixture was hydrogenated at 50 psi on a Parr apparatus for 4 hrs. The reaction was filtered thru Celite, washed with MeOH and the filtrate was concentrated in vacuo to afford 10 mg of the title compound as an oil. Mass Spectrum (NH3 -CI): 507 (M+1).

Workup

  1. filtrationThe reaction was filtered thru Celite
  2. washwashed with MeOH
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cb6188cebeea4271a3b4f4a9305185a6
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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