Hydrochloric Acid → HCID 59403453, compound

Participants

Reaction Steps

Through a solution of 2-(3-buten-1-yl)-3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)benzonitrile (Preparation 22) (8.26 g, 20.97 mmol) in DCM (125 ml) under Ar at −78° C. was bubbled Ar then O2 (5 min each). The ozonoliser (model 502; 75 lh−1; 0.3 A) was switched on and the orange solution ozonolised until it had turned an opaque green-grey colour (3 hrs). The ozonoliser was switched off, and O2, then Ar bubbled though the solution (10 min each). The solution was allowed to warm to RT under Ar, then concentrated in vacuo to give an opaque yellow oil. This was redissolved in dry THF (200 ml), BH3.DMS (9.96 ml, 105 mmol) added (CARE: gas evolution), and the solution stirred at RT for 18 hrs and then at 40° C. for 3 hrs. The reaction was cooled to 0° C., then 0.1M aqueous HCl (150 ml) was added cautiously (CARE: gas evolution), then allowed to stir at RT for 18 hrs. The solution was passed directly down an SCX-2 column (50 g), washing with MeOH. The product was eluted with 0.5M NH3 in MeOH; concentration in vacuo gave an orange foam 3-[2-(aminomethyl)-6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)phenyl]-1-propanol (2.73 g, 3.95 mmol, 18.9% yield). 1H NMR (400 MHz, CDCl3) δ (inter alia) 8.23 (1H, d), 8.05 (1H, dd), 7.86 (1H, d), 7.46 (1H, d), 7.34 (1H, t), 7.06 (1H, d), 4.72 (1H, sept), 4.03 (2H, s), 3.47 (2H, t), 3.27 (2H, t), 1.78 (2H, quin), 1.45 (6H, d); MS (ES) C21H2435ClN3O3 requires 401; found 402 [M+H]+.

Provenance & Evidence