Reaktion #74830

Reaktionsgleichung

acetic acid

5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone

compound ( 2-b )

5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone

sodium borohydride

→

compound ( 1-b )

2-tert-butoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution is refluxed for one hour
2. 2
   workup.ADDITIONis added to the reaction mixture
3. 3
   EinengenThe resulting mixture is concentrated in a vacuum
4. 4
   workup.DISTILLATIONThe residue is distilled in a vacuum

Vorschrift

A 740 mg quantity of 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone (compound (2-b)) and 120 mg of sodium borohydride are dissolved in 100 ml of methanol, and the solution is refluxed for one hour. On completion of the reaction, 2 ml of acetic acid is added to the reaction mixture. The resulting mixture is concentrated in a vacuum. The residue is distilled in a vacuum, giving 2-tert-butoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol (compound (1-b), R1 =t-Bu, R2 =CH3) in a yield of 98.5%, b.p. 75°-79° C./0.005 mm Hg.

Quelle