Hydrochloric Acid → (1R,5R)-1-(3-Methyl-1,2,4-oxadiazol-5-yl)-3-azabicyclo[3.1.0]hexane

Temperature

50 °C

2.5 M HCl (4.5 mL, 0.0113 mol) was added to (1R,5R)-tert-butyl 1-(3-methyl-1,2,4-oxadiazol-5-yl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (143) (0.75 g, 0.0028 mmol) in 4 mL of ethanol. The solution was heated to 50° C. for 2.5 hours, cooled and condensed to a white solid. The material crystallized from 5 mL hot ethanol and 20 mL t-butyl methyl ether. The solids were isolated by filtration and washed with t-butyl methyl ether (2×5 mL) and dried under vacuum over night to 0.48 g white crystalline solid. The optical purity (99.68%) was determined by HPLC analysis (Chiral Technologies Chiral-AGP, 4.0 mm×150 mm, 0.5% methanol, 20 mM sodium phosphate pH=7). MS (ESI) m/z 166 [M+H]+. 1H NMR (DMSO-d6) δ 1.66-1.69 (m, 1H), 1.73-1.76 (m, 1H), 2.31 (s, 3H), 2.47-2.49 (m, 1H), 3.37-3.41 (m, 2H), 3.70-3.74 (m, 2H).

1. temperaturecooled
2. customcondensed to a white solid
3. customThe material crystallized from 5 mL hot ethanol and 20 mL t-butyl methyl ether
4. customThe solids were isolated by filtration
5. washwashed with t-butyl methyl ether (2×5 mL)
6. dry with materialdried under vacuum over night to 0.48 g white crystalline solid

ORD record

ord-df65aa40d38946b586403b987974711c

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174972B2