Hydrochloric Acid → (+/-)-1-(8-Amino-6-azaspiro[3.4]octan-6-carbonyl)cyclopropanecarbonitrile

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Reaction Steps

A solution of (+/−)-tert-butyl (6-(1-cyanocyclopropanecarbonyl)-6-azaspiro[3.4]octan-8-yl)carbamate (0.190 g, 0.595 mmol) in HCl (4.0 M in dioxane) (2.0 mL, 8.00 mmol) was stirred @ r. t. for 50 minutes. +/−MS analysis after 50 min indicated that no starting material could be detected (m/e 220.2, M+H for desired product). The HCl/dioxane was removed under vacuum, and co-evaporated with ether. Additional ether was added to the flask and then decanted off. The ether wash was repeated, and the residual ether was removed under vacuum to afford 0.172 g of the hydrochloride salt of the title compound as a tan, hygroscopic solid. +/−MS: m/e 220.2 (M+H). 1H NMR (400 MHz, DMSO-d6) δ 8.44 (br. s., 2H), 3.74 (br. s., 1H), 3.58-3.49 (m, 1H), 3.45-3.34 (m, 2H), 2.95 (s, 3H), 2.36-2.22 (m, 1H), 2.09-1.92 (m, 2H), 1.91-1.81 (m, 3H)

Provenance & Evidence