Tetrahydrofuran → HCID 66591138, compound

HRID 2363525Notes

Reaction equation

[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)(=[O:19])=[O:18])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1C=CC=[CH:4][CH:3]=1.[O:30]1CCCC1>[OH-].[OH-].[Pd+2]>[OH:30][CH2:4][CH2:3][CH2:2][CH2:1][N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)(=[O:19])=[O:18])[CH2:14][CH2:15][C@H:10]2[CH2:9]1

Participants

Conditions

Temperature: 50 °C

Procedure

N-((3aS,4S,6aR)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-yl)-3-(trifluoromethyl)benzenesulfonamide (0.4237 g, 0.998 mmol) from Step A in tetrahydrofuran (10 mL) was added to 20% palladium hydroxide on carbon (wet, 0.085 g, 0.603 mmol) in a 50 mL pressure bottle under nitrogen. The reaction mixture was then placed under a hydrogen atmosphere (30 psi) and shaken at 50° C. for 18 hours. The mixture was filtered through a nylon membrane and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane supplied the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.50 (s, 1H), 8.38 (d, J=7.9, 1H), 7.85 (d, J=7.8, 1H), 7.68 (t, J=7.8, 1H), 3.89 (dd, J=8.4, 14.2, 1H), 3.82 (t, J=6.2, 2H), 2.82 (dd, J=3.3, 9.7, 1H), 2.62 (qd, J=3.4, 7.9, 1H), 2.42-2.36 (m, 1H), 2.32 (d, J=4.5, 2H), 2.26 (dd, J=6.8, 11.7, 2H), 2.10 (t, J=8.7, 1H), 1.91-1.82 (m, 1H), 1.74-1.67 (m, 2H), 1.64-1.49 (m, 5H), 1.32 (dd, J=6.1, 9.6, 1H); MS (ESI+) m/z 407 (M+H)+.

Workup

filtrationThe mixture was filtered through a nylon membrane
customthe solvent was removed in vacuo
customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record: ord-3566eb85207a4fa79136908596364923
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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