2,6,6-Trimethylbicyclo[3.1.1]heptane-1,2-diol → HCID 86747608, compound

Participants

Reaction Steps

3-Methoxy-1-propene (6.0 g, 83.3 mMol) is reacted with catecholborane (10.0 g, 83.3 mMol) at 100° C. over 24 hr. The crude product is distilled in vacuo to give 3-methoxy-propane-1-boronate as a colourless oil. (+)-Pinanediol(10.6 g, 62.5 g mMol) is dissolved in THF and the above synthesized 3-methoxy-propane-1-boronate (12.0 g, 62.5 mMol) is added. After 1 hr at room temperature, the THF is removed in vacuo and the residue is purified by flash chromatography (80:20 hexane/EtOAc) to give (+)-pinanediol-3-methoxy-propane-1-boronate as a colourless oil.

Provenance & Evidence