Butanal → HCID 178448434, compound

Participants

Reaction Steps

A solution of Example 391 (0.23 g, 0.7 mmol) and butyraldehyde (1 g, 14 mmol) in 1:4 AcOH/CH2Cl2 (25 mL) was stirred at rt for 1 hr. NaBH(OAc)3 (3.0 g, 14 mmol) was added and stirring was continued for 14 hrs. The reaction was quenched with conc. NH4OH and diluted with 10% iPrOH in CH2Cl2 (50 mL). The organic phase was washed with 1 N NaOH (2×20 mL), dried over Na2SO4 and evaporated to give a yellow solid (0.4 g) which was purified by reverse phase preparative HPLC (gradient of aqueous methanol with 0.1% TFA) and converted to the HCl salt by lyophilizing with 1N HCl to give Example 392 as a yellow solid (45 mg, 12%).

Provenance & Evidence