1-Methylimidazole → HCID 10674302, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 9-fluorenylmethyl chloroformate (97%, 270 mg, 1.01 mmol) in dry CH2Cl2 (20 mL) was treated with 1-methylimidazole (90 mg, 1.10 mmol), followed by the above amine (270 mg, 0.84 mmol). The mixture was stirred at 20° C. for 1.5 h, then treated with additional 1-methylimidazole (18 mg, 0.22 mmol) and 9-fluorenylmethyl chloroformate (54 mg, 0.20 mmol). The mixture was stirred for a further 3 h and was then concentrated under reduced pressure, and the residue was chromatographed on silica gel. Elution with CH2Cl2 /petroleum ether (9:1) gave a solid that was recrysallized from iPr2O/petroleum ether to give give 3-(tert-butyloxycarbonyl)-1-(chloromethyl)-5-(9-fluorenylmethyloxycarbonylamino)-1,2-dihydro-3H-benz[e]indole (417 mg, 89%), mp 103-106° C. 1H NMR [(CD3)2SO] δ 9.73 (s, 1 H, NHCO2), 8.21 (br s, 1 H, H-4), 7.98 (d, J=8.5 Hz, 1 H, ArH), 7.95-7.85 (m, 3 H, ArH), 7.76 (br s, 2 H, ArH), 7.54 (t, J=7.5 Hz, 1 H, ArH), 7.48-7.27 (m, 5 H, ArH), 4.46 (d, J=7.0 Hz, 2 H, aliphatic H), 4.32 (t, J=6.8 Hz, 1 H, aliphatic H), 4.26-4.11 (m, 2 H, aliphatic H), 4.11-3.97 (m, 2 H, CHHCl, aliphatic H), 3.88 (dd, J=10.7, 6.9 Hz, 1 H, CHHCl), 1.52 (s, 9 H, C(CH3)3).

Provenance & Evidence