Sodium hydride → HCID 20680633, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-oxopyrrolidin-3-(S)-yl)-carbamic acid benzyl ester (0.15 g, 0.64 mmol) in 6 mL of 10:1 THF:DMF at 0° C. is added a 60% NaH dispersion (0.03 g, 0.71 mmol) followed by 1-phenoxy-6-bromomethyl-isoquinoline (0.2 g, 0.64 mmol). After 16 hours, the solution is treated with 10 mL of saturated NH4Cl. The solution is diluted with CH2Cl2. The organic layer is washed with H2O and saturated NaCl. The resulting product is suspended in 5 g of NH4OAc and heated to 120° C. After 36 hours, the solution is cooled to ambient temperatures. The solution is diluted with H2O and CH2Cl2. The organic layer is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography eluting with 5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2 to give the product as a white solid (0.043 g, 0.11 mmol).

Provenance & Evidence