Cyclohexyl-{(S)-3-[4-hydroxy-4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-4-phenyl-pyrrolidin-1-yl}-acetic acid benzyl ester → 2-cyclohexyl-2-{3-[4-hydroxy-4-(3-phenylpropyl)hexahydro-1-pyridinylmethyl]-4-phenyltetrahydro-1H-1-pyrrolyl}acetic acid

HRID 1386670Notes

Reaction equation

HRID 1386670 reaction equation
[OH:1][C:2]1([CH2:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:7][CH2:6][N:5]([CH2:8][C@@H:9]2[C@@H:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][N:11]([C@H:20]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[C:21]([O:23]CC3C=CC=CC=3)=[O:22])[CH2:10]2)[CH2:4][CH2:3]1.[H][H]>[Pd].CO>[OH:1][C:2]1([CH2:37][CH2:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:7][CH2:6][N:5]([CH2:8][C@@H:9]2[C@@H:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][N:11]([C@H:20]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[C:21]([OH:23])=[O:22])[CH2:10]2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 501044Cyclohexyl-{(S)-3-[4-hydroxy-4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-4-phenyl-pyrrolidin-1-yl}-acetic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 5010462-cyclohexyl-2-{3-[4-hydroxy-4-(3-phenylpropyl)hexahydro-1-pyridinylmethyl]-4-phenyltetrahydro-1H-1-pyrrolyl}acetic acidYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 20 mg (0.032 mmol) 2-(R)-(3-(S)-((4-hydroxy-4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester (from EXAMPLE 1, Step J) and 3 mg of 10% palladium on carbon in 0.5 mL of MeOH was stirred under one atmosphere of hydrogen for 18 h. The reaction was filtered through a 0.45 nylon filter and concentrated to give 16.5 mg (97%) of the title compound: ESI-MS 519 (M+H); HPLC B: 5.07 min.

Workup

  1. filtrationThe reaction was filtered through a 0.45 nylon
  2. filtrationfilter
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c50ee9ed91484d38b41202efc7aa8674
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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