HCID 13190190, compound → HCID 13190193, compound

HRID 1388651Notes

Reaction equation

HRID 1388651 reaction equation
[OH:1][C@H:2]1[CH2:22][C@@:21]2([CH3:23])[C@@H:13]([CH2:14][C@H:15]3[O:26][CH2:25][O:24][C@:16]32[C:17](=[O:20])[CH2:18][OH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:28])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:27])[CH:6]=[CH:5]1>N1C=CC=CC=1.C(OC(=O)CC)(=O)CC>[OH:1][C@H:2]1[CH2:22][C@@:21]2([CH3:23])[C@@H:13]([CH2:14][C@H:15]3[O:26][CH2:25][O:24][C@:16]32[C:17](=[O:20])[CH2:18][O:19][C:2](=[O:1])[CH2:3][CH3:4])[C@H:12]2[C@H:3]1[C@:4]1([CH3:28])[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:27])[CH:6]=[CH:5]1

Participants

4

Reactant 1

HCID 13190190HCID 13190190, compound

Product 1

HCID 13190193HCID 13190193, compoundYield 182.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31263Propionic anhydrideSolvent

Procedure

A solution of 2.4 g of 11β,21-dihydroxy-16α,17α-methylenedioxy-1,4-pregnadiene-3,20-dione in 24 ml of pyridine and 12 ml of propionic acid anhydride is stirred for one hour at room temperature. After precipitation into ice water-sodium chloride, the mixture is filtered off and worked up as usual. The crude product is purified on 220 g of silica gel with a methylene chloride-acetone gradient (0-12% acetone), thus obtaining 2.5 g of 11β-hydroxy-16α,17α-methylenedioxy-21-propionyloxy-1,4-pregnadiene-3,20-dione, mp 184°-185° C.

Workup

  1. customAfter precipitation into ice water-sodium chloride
  2. filtrationthe mixture is filtered off
  3. customThe crude product is purified on 220 g of silica gel with a methylene chloride-acetone gradient (0-12% acetone)

Sources & evidence

ORD record
ord-1af98496eb9d475a990cb60c4417f747
Source dataset
uspto-grants-1984_02
Patent number
US04432976

Reaction notes

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