(Trifluoromethyl)benzene → HCID 86701272, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-benzyloxy-1-methylpyridinium triflate (255 mg, 0.73 mmol), α,α,α-trifluorotoluene (PhCF3, 0.75 mL), MgO (30 mg, 0.74 mmol), and (3S,6S,7R,8R)-3-(tert-butoxycarbonylamino)-8-(2-hydroxyethyl)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (150 mg, 0.36 mmol) was heated at 83° C. for 1 day (d). The reaction mixture was cooled to room temperature (about 22° C.) and filtered through Celite®. The filtrate was concentrated under vacuum and purified by column chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (66 mg, 36%): 1H NMR (300 MHz, CDCl3) δ 7.40-7.21 (m, 5H), 5.28 (m, 2H), 5.06 (t, J=10.0 Hz, 1H), 4.95-4.73 (m, 2H), 4.69 (s, 2H), 4.42 (s, 2H), 3.52-3.33 (m, 3H), 2.77 (td, J=11.5, 2.8 Hz, 1H), 2.60 (dq, J=14.0, 7.0 Hz, 1H), 1.42 (s, 9H), 1.26 (d, J=6.2 Hz, 3H), 1.19 (dd, J=7.0, 2.5 Hz, 6H); ESIMS m/z 530 ([M+Na]+).

Provenance & Evidence