Reaktion #1675631

ord-927dfc136cec4ac6b781829595180b22

Reaktionsgleichung

CCCC(F)(F)C(=O)CCC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC(C)C
15-dehydroxy-17,17-difluoro-13,14-dihydro-16-oxo-PGE2 isopropyl ester
CCCC(F)(F)C(=O)CCC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC(C)C
isopropyl (Z)-7-{(1R)-(2R,3R)-2-(5,5-difluoro-4-oxooctyl)-5-oxo-3-hydroxycylopentyl}-hept-5-enoate
[H][H]
hydrogen
→
CCCC(F)(F)C(=O)CCC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC
titled compound ( 35 )
CCCC(F)(F)C(=O)CCC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC
methyl 7-{(1R)-(2R,3R)-2-(5,5-difluoro-4-oxooctyl)-3-hydroxy-5-oxocylopentyl}heptanoate

Edukte

CCCC(F)(F)C(=O)CCC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC(C)C
15-dehydroxy-17,17-difluoro-13,14-dihydro-16-oxo-PGE2 isopropyl ester
CCCC(F)(F)C(=O)CCC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC(C)C
isopropyl (Z)-7-{(1R)-(2R,3R)-2-(5,5-difluoro-4-oxooctyl)-5-oxo-3-hydroxycylopentyl}-hept-5-enoate
[H][H]
hydrogen

Reagenzien

[Pd]
Pd-C

Lösungsmittel

CCOC(C)=O
ethyl acetate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe reaction mixture was filtered
  2. 2
    Einengenthe filtrate was concentrated
  3. 3
    Sonstigeto give the crude product, which
  4. 4
    Sonstigewas chromatographed on a Rober column

Vorschrift

A solution of 15-dehydroxy-17,17-difluoro-13,14-dihydro-16-oxo-PGE2 isopropyl ester (20) (0.303 g) obtained in Example 3 in ethyl acetate (20 ml) was subjected to hydrogenation with a catalytic amount of 5% Pd-C and hydrogen gas. The reaction mixture was filtered and the filtrate was concentrated to give the crude product, which was chromatographed on a Rober column to give the titled compound (35).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05221799uspto-grants-1993_06