HCID 69686698, compound → HCID 53762810, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,7-dioxo-[1,2]diazepan-1-yl]-acetic acid tert-butyl ester (4) (775 mg, 2.0 mmol) in THF (4 mL) was added borane-THF complex in THF (1M, 4 mL). The reaction was stirred at 0° C. for 30 min then at room temperature for 3 hours. The mixture was diluted with ice-water (60 mL), extracted with ethyl acetate (60 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give a solid, that was purified by flash chromatography using hexane/ethyl acetate (95/5 to 70/30) to afford 585 mg (78% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.43 (s, 9H), 1.78-1.90 (m, 1H), 2.00-2.15 (m, 2H), 2.65-2.78 (m, 1H), 2.95-3.07 (m, 1H), 3.22-3.30 (m, 1H), 3.85-3.92 (d, 1H), 4.30-4.42 (m, 2H), 5.39-5.42 (m, 1H), 7.62-7.71 (m, 2H), 7.79-7.86 (m, 2H). Analytical HPLC: 7.86 min. LC-MS (ES+): m/e=374 (M+H+).

Provenance & Evidence