Methanol → Methyl 1-aminocyclobutane-1-carboxylate hydrochloride

Reaction equation

Cl.[NH2:2][C:3]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[CH3:14][O:8][C:7]([C:3]1([NH2:2])[CH2:6][CH2:5][CH2:4]1)=[O:9]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 113210481-Aminocyclobutanecarboxylic Acid Hydrochloride

Product 1

HCID 42614147Methyl 1-aminocyclobutane-1-carboxylate hydrochlorideYield 98%

Procedure

1-aminocyclobutanecarboxylic acid hydrochloride (5.2 g, 34.5 mmol) and methanol (120 ml) were charged. An ice bath was set and thionyl chloride (3.7 ml, 51.7 mmol) was slowly added thereto. Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours. The resultant product was vacuum-distilled to remove a solvent, and dried in a 60° C. oven so as to obtain methyl-1-aminocyclobutanecarboxylate hydrochloride (5.62 g, 37.1 mmol, 98%).