Crystal structure of (S)-2-[(3S,8S,9S,10R,13S,14S,-17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,-12,13,14,15,16,17-tetradecahydro-1 H-cyclopenta-[a]phenanthren-17-yl]-N-methoxy-N-methylpro-panamide (Fernholz Weinreb amide)

Abstract

The literature compound 3[beta]-hy­droxy-bis­nor-5-cholenic aldehyde is an important inter­mediate for the synthesis of new modulators of the nuclear oxysterol receptor Liver X. As part of our ongoing search for new LXR antagonists, the title compound, C24H39NO3, has proven to be an important inter­mediate in our new synthetic pathway, giving the corresponding aldehyde in high yield and in only three steps from the commercially available 3[beta]-hy­droxy-bis­nor-5-cholenic acid. The title amide crystallized with two mol­ecules in the asymmetric unit, linked into helices by O-H...O hydrogen bonds involving the hy­droxy and carbonyl groups.