Diethyl Ether → PGF1alpha

HRID 903552

Reaction equation

HRID 903552 reaction equation
CCOCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([OH:30])/[CH:12]=[CH:13]/[C@@H:14]1[C@@H:18]([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[C@@H:17]([OH:28])[CH2:16][C@H:15]1[OH:29].[H][H]>[Pd].C(OCC)(=O)C>[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([OH:30])/[CH:12]=[CH:13]/[C@@H:14]1[C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[C@@H:17]([OH:28])[CH2:16][C@H:15]1[OH:29]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 5280363DinoprostHCID 178418361HCID 178418361, compound

Product 1

HCID 5280939PGF1alpha

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Refer to Chart 36. The mixed formula-CC bis(THP ether) of the PGF2α compounds (Example 36, 1.5 g.) in 60 ml. of ethyl acetate are reduced at C5 -C6 by hydrogenation at about 25° C. in the presence of 200 mg. of 5% palladium-on-carbon with slightly over the theory for one equivalent of hydrogen. The solids are filtered off and the filtrate concentrated to yield the corresponding formula-CCXII bis(THP ether) of the PGF1α compounds having Rf 0.28 (TLC on silica gel in acetone-Skellysolve B (1:2)).

Workup

  1. filtrationThe solids are filtered off
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f3f64a85350249b5aaf83abc834347ed
Source dataset
uspto-grants-1980_10
Patent number
US04228104

Linked notes

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