Aniline → HCID 57663775, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-oxo-2a-(2-oxoethyl)-2a,3,4,5-tetrahydropyrrolo[4,3,2-de]quinolin-1(2H)-carboxylate, enantiomer A, (150 mg, 0.474 mmol, described in Intermediate 24) in CH2Cl2 (2 mL) at 0° C. was added DAST (0.125 mL, 0.948 mmol) and the mixture was stirred for 1 h. Additional DAST (0.066 mL) was added and the mixture was stirred for 1 h. To the resulting mixture was added TFA (2 mL) and stirring was continued for 1 h. The mixture was concentrated in vacuo and partitioned between saturated aqueous NaHCO3 (10 mL) and CH2Cl2 (10 mL). The layers were separated and the aqueous layer further extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 95:5, to give the title compound. MS: m/z=239 (M+1).

Provenance & Evidence