Sodium Hydroxide → HCID 86654075, compound

HRID 521000Notes

Reaction equation

[OH-].[Na+].FC(F)(F)C([N:7]1[C@@H:16]2[C@@H:11]([C:12]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[CH:17][C:13]=3[CH2:14][CH2:15]2)[CH2:10][CH2:9][CH2:8]1)=O>O1CCCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:12]3[C@@H:11]4[C@H:16]([CH2:15][CH2:14][C:13]=3[CH:17]=2)[NH:7][CH2:8][CH2:9][CH2:10]4)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 35 °C

Procedure

1 M aqueous NaOH solution (10 mL) is added to a solution of cis-2,2,2-trifluoro-1-[8-(4-methoxy-phenoxy)-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinolin-4-yl]ethanone (0.95 g) in tetrahydrofuran (10 mL) at room temperature. The resulting solution is stirred at 35° C. overnight and then cooled to room temperature. The solution is extracted with ethyl acetate, the combined extracts are washed with brine and dried (Na2SO4). The solvent is evaporated and the residue is chromatographed on silica gel (dichloromethane/methanol containing 1% NH3 95:5→70:30) to give the title compound as a colorless resin-like solid. Yield: 0.64 g (88% of theory); LC (method 1): tR=2.75 min; Mass spectrum (ESI+): m/z=310 [M+H]+.

Workup

temperaturecooled to room temperature
extractionThe solution is extracted with ethyl acetate
washthe combined extracts are washed with brine
dry with materialdried (Na2SO4)
customThe solvent is evaporated
customthe residue is chromatographed on silica gel (dichloromethane/methanol containing 1% NH3 95:5→70:30)

Sources & evidence

ORD record: ord-ff22355466a24688b9a70b5a0c334e19
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328072B2

Reaction notes

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