Triphenylphosphine → HCID 58382158, compound

Participants

Reaction Steps

To a mixture of 4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenol (0.1 g, 0.247 mmol, Prepared using AF from Preparation #AE.1 with (4-tert-butoxyphenyl)magnesium bromide [Novel], AG, J.3 with ethyl formate and L.2 with POCl3) and PPh3 (0.10 g, 0.40 mmol) in THF (1 mL) was added DIAD (0.077 mL, 0.40 mmol). The mixture was stirred at rt for about 20 min and tert-butyl 3-hydroxypyrrolidine-1-carboxylate (0.058 g, 0.31 mmol) was added. The mixture was stirred at rt for about 20 h and the mixture was purified directly by silica gel (25 g) chromatography eluting with a gradient of 40 to 90% EtOAc/DCM to afford tert-butyl 3-(4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenoxy)pyrrolidine-1-carboxylate (0.14 g, 100%): LC/MS (Table 2, Method c) Rt=1.51 min; MS m/z 574 (M+H)+.

Provenance & Evidence