4-Methylmorpholine → HCID 178432701, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of Example 1 (50 mg, 0.14 mmol) and NMM (71 μL, 0.64 mmol) in THF (1 mL) at 0° C. was added a solution of ethyl chloroformate (61 μL, 0.64 mmol) in THF (0.5 mL). The reaction was stirred at 0° C. for ˜3 h, but additional equivalents of NMM and ethyl chloroformate were needed during this time to drive the reaction. The reaction mixture was added dropwise to a solution of NaBH4 in water at 0-5° C. and the combined mixture was stirred for 30 min. The mixture was partitioned between EtOAc and 1M HCl and the organic layer was washed with water, dried through a phase separator and concentrated. The crude was dissolved in DMSO and purified by HPLC (neutral). Freeze-drying of pure fractions gave the title compound (8 mg, 17%) as white powder.

Provenance & Evidence