Sodium borohydride → HCID 118318874, compound

Participants

Reaction Steps

A mixture of (S)-ethyl 2-(2-(((3-allylbenzyl)oxy)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (50 mg, 0.083 mmol) and Grubb's II catalyst (70.2 mg, 0.083 mmol) in DCM (50 mL) was refluxed for 2 h. It was then concentrated. The residue was dissolved in MeOH (2 mL). Sodium borohydride (3.13 mg, 0.083 mmol) was added and the reaction was stirred at rt for 2 h. It was then diluted with NH4Cl, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 20% EtOAc/hexane to isolate ethyl (2S)-2-(tert-butoxy)-2-{4,23-dimethyl-11,22-dioxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.113,17.02,7]nonacosa-2,4,6(29),8,13(28),14,16-heptaen-3-yl}acetate (20 mg, 0.035 mmol, 41.8% yield) as a white solid. LCMS (M+1)=579.7.

Provenance & Evidence