Isopropanol → HCID 86737610, compound

HRID 127857Notes

Reaction equation

HRID 127857 reaction equation
[F:1][C@:2]12[C@@H:24]([OH:25])[CH2:23][C@@:22]3([CH3:26])[C@@H:12]([CH2:13][C@@H:14]([OH:28])[C@:15]3([OH:27])[C:16](=[O:21])[C:17]([O:19][CH3:20])=[O:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:30])[CH:4]=[CH:5][C:6](=[O:29])[CH:7]=1.[C-]#N.[Na+].[CH:34](O)(C)[CH3:35]>>[F:1][C@:2]12[C@@H:24]([OH:25])[CH2:23][C@@:22]3([CH3:26])[C@@H:12]([CH2:13][C@@H:14]([OH:28])[C@:15]3([OH:27])[C:16](=[O:21])[C:17]([O:19][CH2:20][CH2:34][CH3:35])=[O:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:30])[CH:4]=[CH:5][C:6](=[O:29])[CH:7]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 8929Sodium CyanideHCID 86737611HCID 86737611, compound

Product 1

HCID 86737610HCID 86737610, compound

Procedure

A solution of (11β,16α)-9-fluoro-11,16,17-trihydroxy-3,20-dioxopregna-1,4-dien-21-oic acid, methyl ester (1.0 g) in anhydrous isopropyl alcohol (100 ml) containing sodium cyanide (100 mg) is refluxed for 3.0 hours. The isopropanol is then removed by distillation in vacuo and the residue is washed with water, dried and crystallized to afford the title compound.

Workup

  1. temperatureis refluxed for 3.0 hours
  2. customThe isopropanol is then removed by distillation in vacuo
  3. washthe residue is washed with water
  4. customdried
  5. customcrystallized

Sources & evidence

ORD record
ord-70ce152f981c4a4daab53b5c389e1097
Source dataset
uspto-grants-1981_03
Patent number
US04257969

Reaction notes

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