Water → HCID 42599120, compound

Participants

Reaction Steps

A solution of 3-methyl-8H-3a-azacyclopenta[a]indene-1,2-dicarboxylic acid dimethyl ester (3.14 g, 11 mmol) in anhydrous dichloromethane (30 mL) was added dropwise to a stirred suspension of LiAlH4 (1.04 g, 27.5 mmol) in anhydrous ether (45 mL) at 0° C. The mixture was stirred for 15 min after the addition was complete. The excess LiAlH4 was carefully decomposed by the slow, sequential addition of water (1.3 mL), 15% NaOH aqueous solution (1.3 mL), and water (3.6 mL). The solid inorganic salt was removed by filtration and washed with dichloromethane. The combined filtrate and washings was concentrated in vacuo to dryness. The residue was triturated with ether, the solid product was collected by filtration, and dried to give (2-hydroxymethyl-3-methyl-8H-3a-aza-cyclopenta-[a]inden-1-yl)methanol (DA-1090) 1.95 g (77%): mp 123-125° C.; 1H NMR (DMSO-d6) δ 2.53 (3H, s, Me), 3.80 (2H, s, CH2), 4.35 (2H, d, J=5.2 Hz, CH2O), 4.44 (2H, d, J=5.2 Hz, CH2O), 4.47 (1H, t, J=5.2 Hz, exchangeable, OH), 4.61 (1H, t, J=5.2 Hz, exchangeable, OH), 7.07-7.10 (1H, m, Hz, ArH), 7.29-7.33 (1H, m, ArH), 7.46-7.48 (2H, m, 2×ArH). Anal. Calcd. for C14H15NO2: C, 73.34; H, 6.59; N, 6.11. Found: C, 73.08; H, 6.59; N, 6.04.

Provenance & Evidence