Reaktion #725808

Reaktionsgleichung

(1R,2S,3S)-2-benzyloxymethyl-3-methoxycarbonylmethyl-1-(2-tetrahydropyranyloxy)cyclopentane

DIBAL

aluminum hydroxide

magnesium sulphate

→

title compound

Ausbeute 78.6%

(1R,2S,3S)-2-benzyloxymethyl-3-(2-hydroxyethyl)-1-(2-tetrahydropyranyloxy)cyclopentane

Ausbeute 78.6%

Lösungsmittel

methanol

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGThe solution was stirred at room temperature
3. 3
   FiltrationThe mixture was filtered
4. 4
   Einengenthe filtrate was concentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by column chromatography on silica gel using
6. 6
   workup.ADDITIONa mixture of cyclohexane and ethyl acetate (2:1) as eluent

Vorschrift

In a flow of argon, to a solution cooled to -15° C., of 14.2 g of (1R,2S,3S)-2-benzyloxymethyl-3-methoxycarbonylmethyl-1-(2-tetrahydropyranyloxy)cyclopentane (prepared in Reference Example 3) in 100 ml of dry toluene, 42 ml of a 25% solution of DIBAL (diisobutyl aluminium hydride) in toluene was added dropwise. The mixture was stirred for 2 hrs, and then 20 ml of methanol was added thereto at the same temperature. The solution was stirred at room temperature and, after deposition of aluminum hydroxide, magnesium sulphate was added thereto. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 10.3 g of the title compound having the following physical characteristics.

Quelle