2-(R)-(3-(S)-((4-(3-Phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester → 2-cyclohexyl-2-{3-phenyl-4-[4-(3-phenylpropyl)hexahydro-1-pyridinylmethyl]tetrahydro-1H-1-pyrrolyl}acetic acid

HRID 1386721Notes

Reaction equation

HRID 1386721 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:20][N:19]([C@H:28]([CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)[C:29]([O:31]CC4C=CC=CC=4)=[O:30])[CH2:18]3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].CO>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:20][N:19]([C@H:28]([CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)[C:29]([OH:31])=[O:30])[CH2:18]3)[CH2:14][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 1317228082-(R)-(3-(S)-((4-(3-Phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester

Product 1

HCID 5010552-cyclohexyl-2-{3-phenyl-4-[4-(3-phenylpropyl)hexahydro-1-pyridinylmethyl]tetrahydro-1H-1-pyrrolyl}acetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 37 mg (0.062 mmol) of 2-(R)-(3-(S)-((4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, benzyl ester (from EXAMPLE 71, Step A) and 19 mg (0.093 mmol) of 10% palladium on carbon in 4 mL of MeOH was hydrogenated (40 psi) on a Parr shaker for 1 h. The reaction mixture was filtered through a 0.45 micron nylon membrane polypropylene filter and concentrated to give 31 mg (100%) of the title compound: 1H NM (500 MHz) δ 0.85-4.11 (35H), 7.11-7.39 (10H); NH3-CI-MS 503 (M+H).

Workup

  1. customfor 1 h
  2. filtrationThe reaction mixture was filtered through a 0.45 micron nylon membrane polypropylene
  3. filtrationfilter
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-581331d39318414cacafa7043f25e950
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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