Hydrochloric Acid → HCID 58089833, compound

Participants

Reaction Steps

tert-Butyl 1′-(8-azabicyclo[3.2.1]octan-3-yl)-1H-spiro[isoquinoline-4,4′-piperidine]-2(3H)-carboxylate 4c (205 mg, 0.5 mmol) was suspended in Et2O (10 mL) and treated with the (R)-tetrahydrofuran-3-yl carbonochloridate (150 mg, 1 mmol) and triethylamine (0.21 mL, 1.5 mmol, 3 eq). The reaction was stirred at room temperature for 30 min and was then treated with 1N aq. HCl. The phases were separated, the aqueous phase was brought to a basic pH by adding solid KOH, and the resulting suspension was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated to provide crude tert-butyl 1′-(8-(((R)-tetrahydrofuran-3-yloxy)carbonyl)-8-azabicyclo[3.2.1]octan-3-yl)-1H-spiro[isoquinoline-4,4′-piperidine]-2(3H)-carboxylate 4d as a colorless, viscous oil (230 mg, 88% yield). LC/MS m/z [M+H]+ 526.2, retention time 2.54 min (10-99% CH3CN—H2O gradient, with 0.05% TFA, 5 min.

Provenance & Evidence