HCID 69422250, compound → HCID 69419899, compound

HRID 1178873Notes

Reaction equation

HRID 1178873 reaction equation
[ClH:1].C([O:9][C:10]1[CH:11]=[C:12]([S:16]([N:19]([CH3:32])[C@H:20]2[CH2:24][CH2:23][C@@H:22]([N:25]3[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]3)[CH2:21]2)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[ClH:1].[OH:9][C:10]1[CH:11]=[C:12]([S:16]([N:19]([CH3:32])[C@H:20]2[CH2:24][CH2:23][C@@H:22]([N:25]3[CH2:26][CH2:27][CH:28]([CH3:31])[CH2:29][CH2:30]3)[CH2:21]2)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 69422250HCID 69422250, compound

Product 1

HCID 69419899HCID 69419899, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

cis-3-Benzyloxy-N-methyl-N-(3-(4-methylpiperidin-1-yl)cyclopentyl)benzenesulfonamide hydrochloride (Example 8) (64.7 mg, 0.135 mmol) in methanol (10 ml) was hydrogenated over 20% palladium hydroxide on carbon (38 mg) at 45 psi for 3.5 hours. The mixture was filtered and concentrated in vacuo. Recrystallization from methanol-ethyl acetate gave the title compound (47.3 mg, 90%) as a white solid; δH (400 MHz, CD3OD) 1.00 (3H, d, J 6.4 Hz), 1.44 (2H, m), 1.65-1.82 (5H, m), 1.91 (2H, m), 2.07-2.08 (2H, m), 2.79 (3H, s), 2.90 (2H, m), 3.50 (3H, m), 4.40 (1H, m), 7.04 (1H, m), 7.19 (1H, t, J 2.0 Hz), 7.26 (1H, m), 7.39 (1H, t, J 8.0 Hz); m/z (ES+) 353 ([M+H]+, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customRecrystallization from methanol-ethyl acetate

Sources & evidence

ORD record
ord-a906c6f29d9d4da689b02b08ee3eda8f
Source dataset
uspto-grants-2007_10
Patent number
US07276607B2

Reaction notes

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