Reaktion #74829

ord-c5282019786c43e2ad0bdcea505c5eb3

Reaktionsgleichung

$CC/C=C\CC1(C(=O)OC(C)(C)C)C(=O)C=CC1CC(=O)OC$

5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone

$CC/C=C\CC1(C(=O)OC(C)(C)C)C(=O)C=CC1CC(=O)OC$

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

$CC/C=C\CC1(C(=O)OC(C)(C)C)C(=O)C=CC1CC(=O)OC$

compound ( 2-b )

$CC/C=C\CC1(C(=O)OC(C)(C)C)C(=O)C=CC1CC(=O)OC$

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

sodium borohydride

→

$CC/C=C\CC1(C(=O)OC)C(O)CCC1CC(=O)OC$

compound ( 1-b )

$CC/C=C\CC1(C(=O)OC)C(O)CCC1CC(=O)OC$

2-methoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

Edukte

$CC/C=C\CC1(C(=O)OC(C)(C)C)C(=O)C=CC1CC(=O)OC$

5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone

$CC/C=C\CC1(C(=O)OC(C)(C)C)C(=O)C=CC1CC(=O)OC$

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

$CC/C=C\CC1(C(=O)OC(C)(C)C)C(=O)C=CC1CC(=O)OC$

compound ( 2-b )

$CC/C=C\CC1(C(=O)OC(C)(C)C)C(=O)C=CC1CC(=O)OC$

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

sodium borohydride

Reagenzien

Keine

Lösungsmittel

methanol

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
Temperaturthe solution is refluxed for one hour

Vorschrift

A 220 mg quantity of 5-methoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone (compound (2-b)) and 60 mg of sodium borohydride are dissolved in 50 ml of methanol, and the solution is refluxed for one hour. The same procedure as in Example 1 is thereafter repeated, affording 2-methoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol (compound (1-b), R1 =R2 =CH3) in a yield of 94.7%, b.p. 74°-78° C./0.01 mm Hg.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04173707uspto-grants-1979_11