Hydrochloric Acid → HCID 86679242, compound

Participants

Reaction Steps

To a stirred suspension of (5R,7R)-4-(5-chlorospiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochloride (10 mg, 0.027 mmol) in DCE (0.5 mL) was added DIEA (0.009 mL, 0.05 mmol). The suspension was shaken until dissolved. Formaldehyde (37% w/w in water, 0.022 mL, 0.27 mmol) was added as a solution in THF (0.15 mL). The reaction was allowed to stir at about room temperature for about 15 minutes at which point Na(OAc)3BH was added and the reaction allowed to stir overnight. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by column chromatography (DCM:MeOH, 8:1) to give the free base, which was taken up in DCM and acidified with 2N HCl in ether. Removal of the solvents under reduced pressure afforded (5R,7R)-4-(5-chloro-1′-methylspiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochloride. LCMS (APCI+) m/z 385, 387 [M+H]+; Rt=2.18 min.

Provenance & Evidence