Sodium Ascorbate → (2S)-ethyl 2-(2-((4-(1-(allyloxy)-2-methylpropyl)-1H-1,2,3-triazol-1-yl)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Participants

Reaction Steps

A mixture of (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(azidomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.15 g, 0.300 mmol), 3-(allyloxy)-4-methylpent-1-yne (0.083 g, 0.600 mmol), Cu(II)SO4.5H2O (7.50 mg, 0.030 mmol) and (+)-sodium L-ascorbate (0.059 g, 0.300 mmol) in MeOH (2 mL) was stirred for 1 h at rt. Then, purified by prep-HPLC to afford (2S)-ethyl 2-(2-((4-(1-(allyloxy)-2-methylpropyl)-1H-1,2,3-triazol-1-yl)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.0761 g, 0.119 mmol, 39.7% yield) as pale yellow paste. LCMS (M+H)=638.7.

Provenance & Evidence