Cesium carbonate → (5R,7R)-4-(1'-benzyl-4-((tert-butoxycarbonylamino)methyl)spiro[indoline-3,3'-pyrrolidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of (5R,7R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (0.110 g, 0.330 mmol), tert-butyl (1′-benzylspiro[indoline-3,3′-pyrrolidine]-4-yl)methylcarbamate (0.130 g, 0.330 mmol), Cs2CO3 (0.162 g, 0.496 mmol), and Xantphos (28.7 mg, 0.050 mmol) in toluene (2.00 mL) was degassed by bubbling a stream of nitrogen through the solution. Pd(OAc)2 (7.42 mg, 0.0330 mmol) was then added to this solution, and the resulting mixture was heated overnight at 100° C. The reaction mixture was concentrated and purified by Analogix chromatography (DCM/5% MeOH/1% NH4OH) to give (5R,7R)-4-(1′-benzyl-4-((tert-butoxycarbonylamino)methyl)spiro[indoline-3,3′-pyrrolidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (180 mg, 261 mmol, 79%). LCMS (APCI+) M+H+ 692 (100%); Rt=4.89 min.

Provenance & Evidence