Iodoethane → HCID 86680454, compound

HRID 240447Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]3[CH2:17][C@H:18]([OH:20])[CH2:19][C@H:13]3[CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].[H-].[Na+].I[CH2:28][CH3:29]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]3[CH2:17][C@H:18]([O:20][CH2:28][CH3:29])[CH2:19][C@H:13]3[CH2:12]2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:21]([F:22])([F:23])[F:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To (7R,8aS)-2-{[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}octahydropyrrolo[1,2-a]pyrazin-7-ol (0.3 mmol, Example 187) in tetrahydrofuran (1 mL) at room temperature was added NaH (20 mg, 60% in mineral oil). After 15 minutes, iodoethane (0.39 mmol) was added. The mixture was stirred at 60° C. for 2 days. The mixture was partially purified by chromatography on silica gel (CH2Cl2/CH3OH=10:1) to give the title compound as an impure solid (77 mg). The product was purified by HPLC (Gilson®, Xbridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol (70:30 to 0:100 gradient over 16 minutes), flow rate 36 mL/minute, UV=220 nm) to give the title compound (20 mg, 16% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.07 (m, 3H), 1.47 (m, 1H), 1.73 (m, 1H), 2.00 (m, 1H), 2.08 (m, 1H), 2.19 (m, 1H), 2.39 (m, 6H), 2.93 (m, 1H), 3.63 (m, 1H), 3.76 (m, 1H), 3.92 (m, 1H), 8.04 (m, 3H); MS (ESI) m/z 469 (M+H)+.

Workup

customThe mixture was partially purified by chromatography on silica gel (CH2Cl2/CH3OH=10:1)

Sources & evidence

ORD record: ord-841f1cf67ab348b3b4cb9919386e1920
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648074B2

Reaction notes

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