Sodium hydride → HCID 58980801, compound

Participants

Reaction Steps

A mixture of [(2S)-1-methylpyrrolidin-2-yl]methanol (11.5 g, 0.10 mol), DMF (150 mL) and NaH (4.0 g, 60% in mineral oil, 0.1 mol) was agitated for 30 minutes under an atmosphere of nitrogen. A DMF (100 mL) solution of 1-chloro-2-methoxy-4-nitrobenzene (18.7 g, 0.10 mol) was added and the mixture agitated overnight at RT. The mixture was concentrated, diluted with ethyl acetate, extracted three times with water, dried, filtered, then concentrated to give the product as a tan oil (16.78 g, 63%). LCMS m/z 267 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 7.88 (d, 1H), 7.73 (s, 1H), 7.19 (d, 1H), 4.06 (m, 2H), 3.88 (s, 3H), 2.80 (m, 1H), 2.60 (m, 1H), 2.36 (s, 3H), 2.20 (m, 1H). 1.90 (m, 1H), 1.67 (m, 3H) ppm.

Provenance & Evidence