Isopropylethanediol → HCID 86614064, compound

Participants

Reaction Steps

To methyl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a-,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (Preparation 118, 0.20 g, 0.67 mmol) was added toluene (10 ml) titanium (IV) ethoxide (0.07 ml) and 2-isopropoxy ethanol. The reactants were stirred together and then heated under reflux for 1 h, before concentrating in vacuo. The crude residue was purified using a Sep Pak cartridge eluting with hexane and then hexane:ethyl acetate (50:50). Further purification by preparative HPLC was performed using a Magellan column 212×150 mm, flow rate 20 ml/min, eluting with a gradient of water:acetonitrile (55:45 to 90:10) over 8 min to yield the title compound (63.9 mg).

Provenance & Evidence