L-Prolinol → HCID 69282494, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.5 g (11.5 mmol) of 4-chloro-7-iodo-2-methylquinoline and 2.92 g (28.8 mmol) of (S)-2-(hydroxymethyl)pyrrolidine in 1-methyl-2-pyrrolidone (50 ml) was heated at 100° C. (oil bath temperature) for 24 h under an argon athmosphere. In order to complete the reaction, 2.2 ml of (S)-2-(hydroxymethyl)pyrrolidine were added and the solution was heated at 100° C. for further 24 h under argon. The solution was then concentrated in a vacuo (4 mbar) at 100° C. The residue was applied to silica gel column with CH2Cl2/MeOH/NH4OH (95:5:0.2) as eluent. Combination of the purified fractions and concentration in vacuo gave 2.7 g (64%) of the desired (S)-[1-(7-iodo-2-methyl-quinolin-4-yl)-pyrrolidin-2-yl]-methanol as light brown solid. ISP mass spectrum, m/e: 369.1 (M+1 calculated for C15H17IN2O: 369).

Provenance & Evidence