Butyl ether → HCID 11573332, compound

Participants

Reaction Steps

Intermediate 13a (0.5 mmol) from above was dissolved in anhydrous tetrahydrofuran (1.0 mL) and treated with 2.0 eq methylmagnesium bromide in butyl ether (1.0 mL 1.0 M solution, 1.0 mmol). The vial was flushed with nitrogen and stirred at room temperature for 3 h. The reaction was diluted with ethyl acetate (5.0 mL), quenched with saturated aqueous ammonium chloride (1.0 mL) and stirred overnight at room temperature. The organic layer was separated, concentrated in vacuo, then dissolved in methanol:acetonitrile (3.0 mL, 1:1 v/v) and subjected to reverse-phase HPLC purification (5-50% CH3CN/0.08% TFA) to yield 4-(5-chloro-2-methoxyphenyl)-1-(1-methylcyclo-hexyl)piperidine (compound no. 300) as the TFA salt. LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 322.0 [M+H]+, retention time 2.39 min.

Provenance & Evidence