Aluminium lithium hydride → HCID 68593921, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of lithium aluminum hydride (0.059 g, 1.5 mmol) in THF (30 mL) was added ethyl 2-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetate (0.4 g, 1.3 mmol) in THF (10 mL) drop wise at 0° C. The reaction mixture was further heated at 100° C. for 6 h. Reaction was monitored by TLC and LCMS. On completion of the reaction, reaction mixture was quenched with H2O:NaOH:H2O (1:1:3) and the contents were filtered. The filtrate obtained was extracted with Ethyl acetate. Combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to obtain crude product (300 mg). 100 mg of the crude was purified by preparative TLC to obtain 5 mg of 2-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)ethanol as free base. The free base (0.015 g 0.056 mmol) was further dissolved in THF (2 mL), oxalic acid (0.007 g, 0.056 mmol) in THF (1 mL) was added to it and the resulting mixture was further stirred for 30 min at room temperature. The precipitate obtained was filtered and dried under vacuum to afford 20 mg of 2-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)ethanol as an oxalate salt. 1H NMR (CD3OD) 7.45 (s, 1H), 7.4 (d, 1H), 7.1 (d, 1H), 4.3 (s, 2H), 4.2 (t, 2H), 3.9 (t, 2H), 3.5 (t, 2H), 3.2 (t, 2H), 2.9 (s, 3H).

Provenance & Evidence