Potassium bisulfate → HCID 22744159, compound

Participants

Reaction Steps

To a suspension of 3-(9H-Fluoren-9-ylmethoxycarbonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (4.57 g, 10.04 mmol) in Ethyl ether (30 mL) at −5° C. was added dropwise 0.5 equiv of 1.0M Lithium aluminum hydride (LAH) in ethyl ether (5.02 mL, 5.02 mmol). After stirring at −5° C. to room temperature for 1 hr, the reaction mixture was treated with 5% KHSO4 (200 mL), stirred for 5 min and then partitioned between EtOAc/water. The organic phase was washed with saturated NaCl solution (200 mL), dried over Na2SO4 and evaporated to dryness. The residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (20%) to give the title compound (2.18 g, 55%) as a clear oil. TLC (30% EtOAc/Hexane) Rf=0.35; 1HNMR (CDCl3) δ 9.65 (s, 1H), 7.77 (d, J=7.2 Hz, 2H), 7.50 (d, J=7.5 Hz, 2H), 7.41 (t, J=7.5 Hz, 2H), 7.33 (dt, J=7.5, 1.2 Hz, 2H), 5.88 (d, J=7.2 Hz, 1H), 4.50–4.36 (m, 2H), 4.24 (t, J=6.6 Hz, 1H), 3.54–3.45 (m, 1H), 3.00–2.93 (dd, J=17.4, 4.8 Hz, 1H), 2.82–274 (dd, J=17.7, 5.1s Hz, 1H), 1.45 (s, 9H). MS(ES) for C23H25NO5 (MW=395.45): positive 396 (MH+).

Provenance & Evidence