[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([C:11]([NH2:13])=[O:12])[CH2:10][CH2:9][CH2:8]1.C1(C(Cl)=O)CCC1.N>C(OCC)C>[NH2:13][CH2:11][CH:7]1[CH2:10][CH2:9][CH2:8]1.[CH:7]1([C:11]([NH2:13])=[O:12])[CH2:10][CH2:9][CH2:8]1(Aminomethyl)cyclobutane was prepared by lithium aluminum hydride reduction of cyclobutanecarboxamide according to the procedure of Shatkina, T. N.: Reutov, O. A., Dokl. Akad. Nauk. SSSR. (1975) 219:1148 [Chem. Abs. 82: 139453m]. Cyclobutanecarboxamide was prepared as follows: a solution of commercially available cyclobutanecarboxylic acid chloride (10 g) in ethyl ether (500 ml) was stirred at 0° while ammonia gas was introduced, resulting in a white precipitate. This material was collected by filtration and redissolved in 50 ml of ethanol/water (4:1, v/v). This solution was applied to a column containing 75 grams of AG 1-X8 ion exchange resin (hydroxide ion form) (obtained from Bio-Rad Company), and elution was continued with ethanol (1 liter). Evaporation of the eluate provided a quantitative yield (8.36 g) of cyclobutanecarboxamide.
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