Sodium borohydride → HCID 118318892, compound

Participants

Reaction Steps

A mixture of (S)-ethyl 2-(2-(((2-allyl-4,5-difluorobenzyl)oxy)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (100 mg, 0.156 mmol) and Grubbs II catalyst (13.25 mg, 0.016 mmol) in DCM (100 mL) was refluxed for 2 h. It was then concentrated and the residue was dissolved in MeOH (2 mL). Sodium borohydride (5.90 mg, 0.156 mmol) was added and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with EtOAc. The organic layer was washed with water, dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 20% EtOAc/hexane to isolate ethyl (2S)-2-(tert-butoxy)-2-{15,16-difluoro-4,24-dimethyl-11,23-dioxa-1,5,7,8-tetraazapentacyclo[22.2.2.16,9.02,7.013,18]nonacosa-2,4,6(29),8,13(18),14,16-heptaen-3-yl}acetate (60 mg, 0.098 mmol, 62.5% yield) as a white solid. LCMS (M+1)=615.3.

Provenance & Evidence