Methanol → HCID 118342875, compound

Participants

Reaction Conditions

Reaction Steps

A mixture (R)-3,5-dichloro-4((4,4-diallylpyrrolidin-2-yl)methyl)pyridine (3.1 g, 9.96 mmol) and grubbs catalyst 2nd generation (1.691 g, 1.992 mmol) in DCM (996 ml). The mixture was stirred at 40° C. for 20 h. The mixture was concentrated and absorbed onto a plug of silica gel and purified by chromatography through a Biotage column (100 g), eluting with a gradient of 1% to 50% 1 M NH3.MeOH in DCM, to provide (R)-3-((3,5-dichloropyridin-4-yl)methyl)-2-azaspiro[4.4]non-7-ene (1.0 g, 3.53 mmol, 35.5% yield) as dark-brown oil. 1H NMR (400 MHz, CDCl3) δ 8.45 (s, 2H), 5.61-5.72 (m, 2H), 3.69-3.82 (m, 1H), 3.25 (br. s., 2H), 3.05 (d, J=10.47 Hz, 1H), 2.89-2.97 (m, 1H), 2.47 (br. s., 2H), 2.23-2.37 (m, 2H), 1.93 (dd, J=6.84, 12.59 Hz, 1H), 1.69-1.82 (m, 1H); LCMS (ESI) m/z 283.0 (M+H)+.

Provenance & Evidence