Reaktion #2070771

Reaktionsgleichung

(4S,R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-[(phenylmethoxy)methyl]-1-cyclopentene-1-carboxylic acid methyl ester

(4S,5R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-[(phenylmethoxy)methyl]-1-cyclopentene-1-carboxylic acid methyl ester

diisobutylaluminum hydride

potassium sodium tartrate

→

title compound

Ausbeute 100.5%

(4S,5R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-[(phenylmethoxy)methyl]-1-cyclopentene-1-methanol

Ausbeute 100.5%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 500-mL 3-necked round bottomed flask, equipped with an argon inlet
2. 2
   workup.ADDITIONwas added slowly
3. 3
   Sonstigethe reaction
4. 4
   workup.STIRRINGThe mixture was stirred for 2 hours
5. 5
   SonstigeThe organic layer was separated
6. 6
   Extraktionthe aqueous layer was extracted with n-hexane (200 mL)
7. 7
   WaschenThe combined organic layer was washed with water (50 mL)
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Einengenconcentrated in vacuo

Vorschrift

A 500-mL 3-necked round bottomed flask, equipped with an argon inlet, a temperature probe, and a mechanical stirrer, was charged with (4S,R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-[(phenylmethoxy)methyl]-1-cyclopentene-1-carboxylic acid methyl ester (7) (10 g, 26.55 mmol, as prepared in Example 9) in DCM (200 mL). The solution was cooled to −78° C. and to this solution diisobutylaluminum hydride (1 M, 66.39 mL, 66.375 mmol in toluene) was added slowly. The reaction mixture was stirred at −78° C. for 2 hours to complete the reaction. The reaction mixture was poured into saturated solution of potassium sodium tartrate (400 mL). The mixture was stirred for 2 hours. The organic layer was separated and the aqueous layer was extracted with n-hexane (200 mL). The combined organic layer was washed with water (50 mL), dried over magnesium sulfate, and concentrated in vacuo to give the title compound (9.3 g) as a yellowish oil.

Quelle