Cyclopropanecarbonyl chloride → HCID 20576981, compound

Participants

Reaction Conditions

Reaction Steps

(±)-cis-4,5,6a,7,8,9,10,10a-octahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole from Example 3 (0.050 g, 0.25 mmol) was dissolved in CH2Cl2 (5 mL) with Et3N (0.75 mL) and cooled to 0° C. The cyclopropanecarbonyl chloride (0.026 g, 0.26 mmol) was then added dropwise. The solution was stirred at 0° C. for 1 h and then warmed to room temperature and stirred for 1 h. The reaction mixture was partitioned between water and CHCl3 (3×15 mL) and the layers separated. The aqueous layer was extracted with CHCl3. The combined organics were washed with brine, H2O and dried (Na2SO4) and evaporated affording a light yellow liquid which was further purified by preparatory silica gel TLC (5% MeOH/CH2Cl2). The title compound was isolated as a clear colorless liquid (0.042 g, 65%). 1H NMR (CD3OD, 300 MHz) δ 7.22-7.58 (m, 3H), 4.62-4.75 (m, 1H), 3.85-4.30 (m, 5H), 3.55-3.62 (m, 2H), 1.9-2.18 (m, 3H), 0.75-0.9 (m, 4H) ppm.

Provenance & Evidence