HCID 54674497, compound → HCID 54674652, compound

HRID 2402750Notes

Reaction equation

[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]([F:27])([F:26])[C:11]1[N:16]=[C:15]([N:17]2[CH2:21][C@@H:20]3[C:22](=[O:25])[CH2:23][CH2:24][C@@H:19]3[CH2:18]2)[CH:14]=[CH:13][CH:12]=1>O1CCCC1>[C:1]1([C@:22]2([OH:25])[C@@H:20]3[C@@H:19]([CH2:18][N:17]([C:15]4[CH:14]=[CH:13][CH:12]=[C:11]([C:10]([F:26])([F:9])[F:27])[N:16]=4)[CH2:21]3)[CH2:24][CH2:23]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Phenylmagnesium bromide in tetrahydrofuran (0.266 mL, 0.266 mmol) was added to (3aR,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]hexahydrocyclopenta[c]pyrrol-4(1H)-one (60 mg, 0.222 mmol) from Example 32 in tetrahydrofuran (1 mL) at −40° C., and the reaction mixture was allowed to warm to −10° C. in 20 minutes. The reaction was quenched with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The combined organic washes were purified by silica gel chromatography using 0-40% ethyl acetate/hexane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.78 (dt, J=8.2, 1.6, 2H), 7.45 (t, J=7.7, 3H), 7.37-7.27 (m, 1H), 6.90 (d, J=7.2, 1H), 6.70 (d, J=0.5, 1H), 6.46 (d, J=8.6, 1H), 4.02-3.94 (m, 1H), 3.92-3.82 (m, 1H), 3.62-3.42 (m, 2H), 3.07 (td, J=9.3, 2.8, 1H), 3.02-2.92 (m, 1H), 2.38-2.22 (m, 2H), 2.17-1.98 (m, 2H); MS (ESI+) m/z 349 (M+H)+.

Workup

customThe reaction was quenched with saturated aqueous ammonium chloride solution
extractionthe mixture was extracted with ethyl acetate
customThe combined organic washes were purified by silica gel chromatography

Sources & evidence

ORD record: ord-59757ff1f8794862bc266c42b8c78db7
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796470B2

Reaction notes

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