Hydrochloric Acid → (+/-)-1-(8-Amino-6-azaspiro[3.4]octan-6-carbonyl)cyclopropanecarbonitrile
Reaction equation
[C:1]([C:3]1([C:6]([N:8]2[CH2:15][CH:14]([NH:16]C(=O)OC(C)(C)C)[C:10]3([CH2:13][CH2:12][CH2:11]3)[CH2:9]2)=[O:7])[CH2:5][CH2:4]1)#[N:2].Cl>>[NH2:16][CH:14]1[C:10]2([CH2:13][CH2:12][CH2:11]2)[CH2:9][N:8]([C:6]([C:3]2([C:1]#[N:2])[CH2:4][CH2:5]2)=[O:7])[CH2:15]1Participants
Procedure
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)
Workup
- wait+/−MS analysis after 50 min indicated that no starting material
Sources & evidence
- ORD record
- ord-9888c46823be4802a4340353f60a910e
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987268B2
Reaction notes
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