Reacción #414501

Ecuación de reacción

ammonium chloride

Methyl (4aS, 7R, 7aR)-1, 4a, 5, 6, 7, 7a-hexahydro-1-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylate

sodium boron hydride

methanol

→

2-[(1R, 2R, 3S)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]ethan-1-ol

Rendimiento 76.3%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was once concentrated under a reduced pressure, and extraction
2. 2
   Otrodried
3. 3
   workup.ADDITIONby adding magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated under a reduced pressure
6. 6
   OtroThe residual substance was purified by chromatography
7. 7
   Otrothe solvent of the fraction obtained from ether
8. 8
   workup.DISTILLATIONethyl acetate=1:1 eluent was distilled
9. 9
   Otroa colorless oily substance was obtained

Procedimiento

Methyl (4aS, 7R, 7aR)-1, 4a, 5, 6, 7, 7a-hexahydro-1-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylate (300 mg, 0.0014 mol) and sodium boron hydride (270 mg, 0.007 mol) were dissolved in 8 ml of tetrahydrofuran, and while the reaction mixture was refluxed at 80° C., 1.5 ml of methanol was added dropwise in the course of 1 hour. The reaction mixture was stirred at the same temperature for 5 hours, and 10 ml of a saturated ammonium chloride solution wad added. The reaction mixture was once concentrated under a reduced pressure, and extraction was made with ethyl acetate (50 ml×2). The organic layers were joined, dried by adding magnesium sulfate, filtered and thereafter concentrated under a reduced pressure. The residual substance was purified by chromatography using silica gel, and the solvent of the fraction obtained from ether:ethyl acetate=1:1 eluent was distilled, and a colorless oily substance was obtained, i.e., 2-[(1R, 2R, 3S)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]ethan-1-ol (169 mg, yield=63.8%). This 2-[(1R, 2R, 3S)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]ethan-1-ol had the following physicochemical properties.

Fuente