Ethanolamine → Dihydrothebaine

Participants

Reaction Conditions

Reaction Steps

Thebaine (142.86 g of 70 wt % material containing 30 wt % water, 100.00 g, 0.321 mol), p-toluene sulfonyl hydrazide (131.58 g, 0.706 mop and ethanol (400 ml) were stirred and heated to 70° C. Ethanol amine (43.16 g, 0.706 mol) was added to this solution over a 1 h period. The reaction was heated for a further 10 h at this temperature and then allowed to cool to room temperature. The reaction was diluted with water (400 ml) and the pH adjusted to >9.30 with concentrated (28.0-30.0%) ammonium hydroxide (30 ml) and cooled to <5° C. The product was isolated by filtration and washed with 1% v/v ammonium hydroxide in water (400 ml) to give 8,14-dihydro-thebaine as a white amorphous solid (91.94 g, 91.3% yield, 99.29 wt % by assay, with 0.16 wt % of the 6-β-parzone methyl ether impurity).

Provenance & Evidence