Dichloromethane → HCID 58911525, compound

Participants

Reaction Conditions

Reaction Steps

1-Chloroethylchloroformate (0.050 ml, 0.47 mmol) was added to a solution of (11aR)-2,3,4,6, 11,11a-hexahydro-2-(2,4-dimethoxybenzyl)-4-methyl-1H-pyrazino[1,2-b]isoquinoline (53 mg, 0.15 mmol) in 1,2-dichloroethane (1 ml) stirring at 0° C. The ice bath was removed and the reaction stirred at ambient temperature for 30 min. After refluxing an additional 2 h, the reaction was evaporated in vacuo. Methanol (1.0 ml) was added to the residue and the reaction refluxed under nitrogen for 1 h. Evaporation in vacuo afforded 75 mg of crude product. This crude product was transferred to a separatory funnel with CH2Cl2 and saturated NaHCO3. Extraction with CH2Cl2 (2×) and drying of the combined organic layers over MgSO4 afforded 42 mg which was further purified by flash chromatography (SiO2, 0.2 to 10% 2N NH3 in MeOH/CH2Cl2) to give pure product (17 mg, 55%). MS (ESI) 203 (M+H).

Provenance & Evidence