Sodium borohydride → HCID 70591639, compound

HRID 1679384Notes

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-acddb03abf8445a994d36315118cd1ce
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04080458

Reaction notes

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