1,2-Dichloroethane → (R)-allyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethylcarbamate

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Reaction Steps

(R)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine was dissolved in DCE (400 uL, 0.1 M in DCE, 40 umol) and potassium carbonate added (100 mg, 723 umol, 18 eq), followed by allyl carbonochloridate (400 uL, 0.2 M in DCE, 80 umol, 2.0 eq). The reaction mixture was agitated at room temperature for 18 h and then filtered and rinsed with DCE (2×250 uL). The combined filtrate was evaporated and the residue was redissolved in 1 mL of MeOH and purified by reverse phase preparative HPLC using MeOH:water:TFA system. (R)-allyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethylcarbamate was obtained as a colorless oil (13.2 umol, 33% yield). LCMS: M+calc=478.11; found=479.35.

Provenance & Evidence