1,2-Dichloroethane → HCID 86669840, compound

Participants

Reaction Steps

To a solution of (3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-amine (HCl salt, 1.2 g, 3.13 mmol), [(tert-butoxycarbonyl)amino]acetic acid (727 mg, 4.15 mmol) in 40 mL pyridine was added EDC (1.06 g, 5.5 mmol). After 16 hours at room temperature, water (10 mL) and CH2Cl2 (10 mL) were added and the organic layer was washed with brine, dried over Mg2SO4, filtered and concentrated. The crude mixture was subjected to flash chromatography to afford tert-butyl [2-({(3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]carbamate (812 mg, 62%). To a solution of tert-butyl [2-({(3R)-1-[1-(4-methoxyphenyl)piperidinyl)pyrrolidin-3-yl}amino)-2-oxoethyl]carbamate (1.00 g, 2.31 mmol) in CH2Cl2 (10 mL) was added 4N HCl/dioxane (10 mL). After 2 hours, ether was added and 2-amino-N-{(3R)-1-[1-(4-methoxyphenyl)piperidin-4-yl]pyrrolidin-3-yl}acetamide (1.02 g, quant.)

Provenance & Evidence