Cesium carbonate → HCID 67490685, compound

Participants

Reaction Steps

To a solution of the product of Step A (59 mg, 0.091 mmol) in NMP (3 mL) was added Cs2CO3 (38.5 mg, 0.118 mmol) then Mel (0.007 mL, 0.1 mmol). After being stirred at RT for one hour, the mixture was diluted with saturated NaCl (act) then extracted twice with EtOAc. The combined organic layers were dried over sodium sulfate, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 0-20% MeOH/DCM, then further purified by PTLC eluting with 50% EtOAc/hexanes to afford the 1-methyl regioisomer (EXAMPLE 2, Step B) as well as the title compound. The title compound was resolved to provide enantiopure material by HPLC on a ChiralPak IA (2 cm×25 cm) column eluting with 9 mL/min of 3% EtOH/n-heptane. LC1 2.83 min. (M-tBu+H)+ 606.

Provenance & Evidence