Aluminium lithium hydride → HCID 42597449, compound

Participants

Reaction Steps

A solution of the 3-(4-chlorophenyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline-1,2-dicarboxylic acid dimethyl ester (5.03 g, 15 mmol) in anhydrous dichloromethane (120 mL) was added dropwise into a stirred suspension of LiAlH4 (1.31 g, 34.5 mmol) in anhydrous diethyl ether (50 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 (2.0 mL), 15% aqueous NaOH (2.0 mL), and water (6.0 mL). The mixture was filtered to remove inorganic salt, the solid residue was washed with hot THF (300 mL). The combined filtrate and washings was evaporated in vacuo to dryness and the solid residue was recrystallized from dichloromethane/ether to give [3-(4-chlorophenyl)-2-hydroxymethyl-5,10-dihydro-pyrrolo[1,2-b]isoquinolin-1-yl]methanol (DA-1116), 3.12 g (61.4%); mp 170-171° C.; 1H NMR (DMSO-d6) δ 4.06 (2H, s, CH2), 4.28 (2H, d, J=5.1 Hz, CH2), 4.50 (2H, d, J=5.1 Hz, CH2), 4.55 (1H, t, J=5.1 Hz, exchangeable, OH), 4.57 (1H, t, J=5.1 Hz, exchangeable, OH), 4.98 (2H, s, CH2), 7.18-7.20 (1H, m, ArH), 7.25-7.30 (2H, m, ArH), 7.36-7.40 (1H, m, ArH), 7.49 (2H, d, J=8.5 Hz, 2×ArH), 7.54 (2H, d, J=8.5 Hz, 2×ArH); m/z 339.82 (M+H)+ Anal. Calcld. for C20H18CINO2: C, 70.69; H, 5.34; N, 4.12. Found: C, 70.42; H, 5.29; N, 4.19.

Provenance & Evidence