Methylamine → HCID 86587926, compound

Participants

Reaction Steps

To a stirred THF solution of methylamine (2 M, 1.01 mL, 4 eq, 2.02 mmol) is added THF (10 mL) solution of (2R,3R,4S,5Z,8S,9R,10R,11S,12S,13Z)-3,9-bis[[(1,1-dimethylethyl) dimethylsilyl]oxy]-11-hydroxy-2,4,6,8,10,12-hexamethyl-5,13,15-hexadecatrienal (300 mg, 0.505 mmol, 1 eq) at 23° C. After stirring for 20 minutes, NaBHAc3 is added followed by addition of 1 drop of AcOH. The solution is stirred for an additional 2 hours and diluted with EtOAc (10 mL), washed with aqueous saturated Na2CO3 (2×5 mL), brine, dried with Na2SO4 and concentrated in vacuo. The residue is purified by flash chromatography (silica gel, gradient 10–30% MeOH/EtOAc) to give the desired compound (180 mg, 59%) as a colorless oil.

Provenance & Evidence