Aluminium lithium hydride → HCID 42597686, compound

Participants

Reaction Steps

A solution of the 3-(4-methoxyphenyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline-1,2-dicarboxylic acid dimethyl ester (3.91 g, 10 mmol) in anhydrous dichloromethane (20 mL) was added dropwise to a stirred suspension of LiAlH4 (0.87 g, 23 mmol) in anhydrous diethyl ether (30 mL) at 10-15° C. The reaction mixture was further stirred for 2 hours after the addition was completed. The mixture was cooled in an ice bath and the excess hydride was destroyed by the sequential addition of water (1.2 mL), 15% aqueous NaOH (1.2 mL), and water (3.6 mL) at 0° C. The inorganic salt was removed by filtration, was washed with hot THF (300 mL), and the combined filtrate and washings was evaporated under reduced pressure to dryness. The solid residue was recrystallized from dichloromethane/ether to give [2-hydroxymethyl-3-(4-methoxyphenyl)-5,10-dihydropyrrolo[1,2-b]-isoquinolin-1-yl]methanol (DA-1106), 2.29 g (68.4%); mp 174-176° C.; 1H NMR (DMSO-d6) δ 3.82 (3H, s, OMe), 4.05 (2H, s, CH2), 4.26 (2H, d, J=5.0 Hz, CH2), 4.45-4.54 (4H, m, CH2 and exchangeable, 2×OH), 4.93 (2H, s, CH2), 7.05 (2H, d, J=8.4 Hz, ArH), 7.17-7.21 (1H, m, ArH), 7.25-7.28 (2H, m, ArH), 7.38 (2H, d, J=8.4 Hz, ArH), 7.37-7.39 (1H, m, ArH); m/z 451.9 (M+H)+ Anal. Calcld. for C21H21NO3 0.2H2O: C, 74.40; H, 6.36; N, 4.13. Found: C, 74.41; H, 6.30; N, 4.13.

Provenance & Evidence