Sodium borohydride → PGF1alpha

Reaktionsgleichung

[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH2:11][C@H:10]1[OH:24].[BH4-].[Na+]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C@@H:12]([OH:13])[CH2:11][C@H:10]1[OH:24].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C@H:12]([OH:13])[CH2:11][C@H:10]1[OH:24]

Komponenten

Edukt 2

HCID 4311764Sodium borohydride

HCID 5280723Alprostadil

Produkt 2

HCID 5280939PGF1alpha

HCID 5283070Prostaglandin F1beta

Versuchsvorschrift

Specifically to formulate the analogue of PGA1, which bears the name of Methyl 15-Hydroxy-9-oxo-16,17,18,19,20-pentanorprosta-10,13E-dien-1-oate (XVI), the depentyl PGE1 (Methyl 11α,15-Dihydroxy-9-oxo-16,17,18,19,20-pentanorprosta-13E-en-1-oate (XV) is mixed with a mild carboxylic acid at a relatively high temperature of about 50° to 70° C. Using acetic acid also gives the 15-acetate (XVII). On the other hand, mixing the same depentyl analogue of PGE1 with sodium borohydride in a dry alcohol at about -20° to +25° C. will produce the depentyl analogues of PGF1α (XVIII) and PGF1β (XIX).