HCID 131722811, compound → HCID 131722810, compound

HRID 1386741Notes

Reaction equation

HRID 1386741 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]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]4[CH2:34][P:35](=[O:52])([O:44]CC4C=CC=CC=4)[O:36]CC4C=CC=CC=4)[CH2:18]3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>CO.[Pd]>[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:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:20][N:19]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]4[CH2:34][P:35](=[O:36])([OH:52])[OH:44])[CH2:18]3)[CH2:14][CH2:15]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 131722811HCID 131722811, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131722810HCID 131722810, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 39 mg (0.054 mmol) 2-(R/S)-(3-(S)-((4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexylmethylphosphonic acid, dibenzyl ester (from EXAMPLE 93, Step D) in 2.3 mL of MeOH was hydrogenated using 17 mg of 10% palladium on carbon under 47 psi of hydrogen gas on a Parr shaker. After TLC indicated the absence of the starting benzyl ester, the reaction was filtered through a 0.45 micron nylon membrane polypropylene filter and concentrated to give 21.1 mg (73%) of the title compound: 1H NMR (500 MHz, CD3OD) δ 0.99-3.57 (m, 35H), 6.97-7.29 (m, 10H); ESI-MS 539 (M+H); HPLC A: 2.59 min.

Workup

  1. filtrationthe reaction was filtered through a 0.45 micron nylon membrane polypropylene
  2. filtrationfilter
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-502a7118a0c0457493ea9b3f4cfdb2d1
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

Loading…