Methanol → HCID 131718832, compound

HRID 1769526Notes

Reaction equation

HRID 1769526 reaction equation
I(O)(=O)(=O)=O.OC[C:8](=[O:30])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C:23](=[CH:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][C@H:10]1C.[CH3:31][OH:32]>O>[CH3:31][O:32][C:8]([C@H:9]1[CH2:10][CH2:11][C@H:12]2[C@H:13]3[C:23](=[CH:24][CH2:25][C@:26]12[CH3:27])[C@:21]1([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3)=[O:30]

Participants

5

Reactant 3

HCID 887MethanolHCID 65185Metaperiodic acidHCID 22842962HCID 22842962, compound

Product 1

HCID 131718832HCID 131718832, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Periodic acid (14.73 g) is dissolved in water (162 ml) and is then slowly added to a stirred solution of 21-hydroxy-16α-methylpregna-4,9(11)-diene-3,20-dione (10.34 g) in methanol (675 ml) at 26°-28°. The reaction mixture is stirred for an additional hour at 20°-25° and then concentrated under reduced pressure with concurrent addition of water (1675 ml). The mixture is cooled and filtered to give 9.94 g of 16°-methylandrosta-4,9(11)-dien-3-one 17β-carboxylate.

Workup

  1. concentrationconcentrated under reduced pressure with concurrent addition of water (1675 ml)
  2. temperatureThe mixture is cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-bbfceea9ab0b45db9e33dd12986e3dee
Source dataset
uspto-grants-1995_01
Patent number
US05380841

Reaction notes

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