4-Bromobutyryl chloride → HCID 11641483, compound

Participants

Reaction Steps

To a solution of 1-(benzyloxy-carbonyl)amino-3,5-dimethyl-7-hydroxyadamantane (100 mg) in DMF (0.4 mL) was added 4-bromobutyryl chloride (0.3 mL). The reaction mixture was stirred for 2 h at room temperature. The mixture was purified by thin layer chromatography eluting with ethyl acetate and hexane (½, v/v) to afford an oily product. 1H NMR (DMSO-d6, ppm): 7.38-7.29 (m, 5 H, C6H5), 7.12 (brs, 1 H, NH), 4.95 (s, 2 H, OCH2), 3.53-3.49 (t, 2 H, J=6.6 Hz, COCH2), 2.36-2.32 (t, 2 H, J=7.7 Hz, CH2Br), 2.10 (s, 2 H), 2.00-1.96 (m, 2 H, CHCH2CH2), 1.66 (s, 4 H), 1.59-1.41 (dd, 4 H, J=11.5, 51.7 Hz), 1.08-1.07 (d, 2 H, J=3.8 Hz), 0.87 (s, 6 H, 2×CH3).

Provenance & Evidence