HCID 86643142, compound → HCID 59396844, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of ethyltriphenylphophonium bromide (0.56 g, 1.5 mmol) in THF (8 mL) cooled at −75° C. was added n-BuLi (1.6 M in hexane, 1.0 mL). To the resulting orange solution was added the product from step 2 (0.24 g, 0.50 mol) in THF (1.0 mL). The reaction mixture was gradually warmed to 25° C. and quenched with acetic acid (0.1 mL). The solvent was removed and the residue was taken up in diethyl ether and filtered through a short column of silica gel. The filtrated was concentrated and the residue was dissolved in THF-t-BuOH (1:1, v/v) (10 mL). The solution was stirred in the presence of Rh(PPh3)3Cl (40 mg) under hydrogen (45 psi) for 18 h. The reaction mixture was concentrated and the residue was purified by preparative HPLC on a RP-18 column using 10-100% acetonitrile in water gradient solvent system modified with 0.1% trifluoroacetic acid to give the title compound.

Provenance & Evidence