Dichloromethane → HCID 69083344, compound

Participants

Reaction Steps

A solution of compound 77 (150 mg, 0.23 mmol) in THF (10 mL) was treated with LiAlH4 (26.6 mg, 0.70 mmol) for 3 h at room temperature. The reaction mixture was then quenched by addition of saturated aqueous NH4Cl (20 mL), extracted with dichloromethane (3×30 mL), and dried over anhydrous magnesium sulfate. The filtrate was concentrated under vacuum to give crude compound 78 as a yellow oil (90 mg), which was dissolved into dichloromethane (10 mL) and treated with TFA (1 mL) overnight at room temperature. Removal of volatiles gave a residue, which was purified by Prep-HPLC with the following conditions: [(Agilent 1200 prep HPLC: Column, Sun fire prep. C18; mobile phase, water with 0.03% trifluoroacetic acid and CH3CN (10% up to 20% in time 10); Detector, 220 nm.)] to give the title compound 79 (Example 143) as a white solid (10.8 mg, 23%). (ES, m/z) [M+H]+ 263.1; 1H NMR (300 MHz, D2O) δ 6.18-6.20 (d, J=6.3 Hz, 1H), 4.08-4.12 (m, 1H), 3.89-3.93 (m, 1H), 3.36-3.51 (m, 4H), 2.74-2.76 (m, 3H), 1.68-1.76 (m, 1H), 1.33-1.62 (m, 3H).

Provenance & Evidence