1,4-Dioxane → (+/-)-6-(Methylsulfonyl)-6-azaspiro[3.4]octan-8-amine

Participants

Reaction Steps

(+/−)-tert-butyl-(6-(methylsulfonyl)-6-azaspiro[3.4]octan-8-yl)carbamate (0.195 g, 0.641 mmol) was dissolved in 4.0 M HCl in dioxane (3.0 mL, 12.00 mmol) and stirred at r. t. for 1 hr 5 min. +/−MS analysis after 50 min. indicated a the reaction had essentially proceeded to completion (m/e 205.2, M+H for desired product; no sm was detected). HCl/dioxane was removed under vacuum, and the residue co-evaporated with ether. The initially obtained oil was dried under vacuum over P2O5 to yield 0.153 g of the HCl salt of the title compound as a pale tan solid. +/−MS: m/e 205.2 (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