Water → HCID 10180362, compound

Participants

Reaction Conditions

Reaction Steps

Part A: 3-aminopyrrolidine (636 mg, 4 mmol), triethylamine (2.7 mL, 20 mmol), and 4-(dimethylamino)pyridine (75 mg) were suspended in acetonitrile. After 10 min, the reaction was chilled to 0° C. 4-methoxybenzoyl chloride (0.54 mL, 4 mmol) was added drop-wise. After 30 min, 2-carboethoxybenzenesulfonyl chloride (0.996 g, 4.0 mmol) was introduced drop-wise by syringe. The mixture was stirred at 0° C. for 1 hr, and then at ambient temperature for 2 hr. Water was added (50 mL). The mixture was extracted using ethyl acetate (2×50 mL). The organic layer was dried over MgSO4, filtered through silica, and concentrated. The residue was purified using silica gel chromatography using 1:1 ethyl acetate:hexane to ethyl acetate as eluant. The desired amide sulfonamide was isolated as a foam (282 mg, 16%).

Provenance & Evidence