Water → HCID 69959107, compound

Participants

Reaction Steps

The alloc protected hydroxy proline (13) (18 g, 83.72 mmol) was dissolved in acetone (1260 ml). The Jone's reagent [Cro3:26.6 g/H2SO4:21.3 ml and the solution was made up to 100 ml with water] (87 ml) was added over 10 min. The resulting mixture was stirred for a further 45 minutes when the excess oxidant was quenched with methanol (15 ml). The green chromium salts were removed by filtration through Celite and the filtrate was diluted in CHCl3(1000 ml). The combined organic phase was washed with brine several times (5×500 ml) and the solvent was evaporated under reduced pressure, to yield the ketone 14 which was used without any purification.

Provenance & Evidence