Sodium borohydride → HCID 70591639, compound

HRID 2057391Notes

Reaction equation

[OH:1][CH:2]1[C@H:15]([S:16][CH2:17][C:18]2([O:27][CH2:26][CH2:25][O:24]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@@H:5]([CH2:6][CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:4](=[O:28])[CH2:3]1.[BH4-].[Na+]>>[OH:28][CH:4]1[CH2:3][CH:2]([OH:1])[C@H:15]([S:16][CH2:17][C:18]2([O:24][CH2:25][CH2:26][O:27]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@H:5]1[CH2:6][CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 70589714HCID 70589714, compound

Product 1

HCID 70591639HCID 70591639, compound

Procedure

0.1 g. 11-hydroxy-15,15-ethylenedioxy-9-oxo-13-thia-5-prostenoic acid is reduced with NaBH4 analogously to Example 14 and the 9,11-dihydroxy-15,15-ethylenedioxy-13-thia-5-prostenoic acid obtained subsequently stirred at room temperature for 2 hours with 10 ml. IN aqueous HCl and 10 ml. dioxan. The reaction mixture is saturated with NaCl extracted with benzene, the organic phase dried and the solvent distilled off to obtain, as the residue, 9,11-dihydroxy-15-oxo-13-thia-5-prostenoic acid.

Sources & evidence

ORD record: ord-52b13516d9194125adc055a9ea6a25f5
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04210651

Reaction notes

Loading…