تفاعل #77530

معادلة التفاعل

hydrogen

[(2R)-7-(benzyloxy)-8-(2-hydroxyethyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

triphenylphosphine

diisopropylazodicarboxylate

→

title compound

2,3.8,9-Tetrahydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-Methylbenzenesulfonate

المذيبات

methanol

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe catalyst was then removed by filtration through celite
2. 2
   تركيزthe filtrate concentrated in vacuum to 1.72 g of a yellow oil
3. 3
   workup.DISSOLUTIONThe oil was dissolved in 100 mL of benzene
4. 4
   أخرىThe solvent was then removed in vacuum
5. 5
   أخرىthe residue column chromatographed on silica gel with methylene chloride as eluant

الإجراء التجريبي

A solution of 2.3 g (4.9 mmole) of [(2R)-7-(benzyloxy)-8-(2-hydroxyethyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate in 100 mL of methanol was added to a slurry of 0.40 g of 10% palladium on carbon in 30 mL of methanol in 500 mL Parr hydrogenation bottle. The mixture was treated with 50 psi of hydrogen on a Parr shaker for 15 hours. The catalyst was then removed by filtration through celite and the filtrate concentrated in vacuum to 1.72 g of a yellow oil. The oil was dissolved in 100 mL of benzene, 2.1 g (8.0 mmole) of triphenylphosphine and 1.6 g (8.0 mmole) of diisopropylazodicarboxylate added and the mixture stirred at room temperature for 3 days. The solvent was then removed in vacuum and the residue column chromatographed on silica gel with methylene chloride as eluant to give 1.25 g of the (R)-enantiomer of the title compound as a white solid, m.p. 95-96° C.

المصدر