Pyridine → 9beta,11beta-Epoxy-3,17,21-triacetoxy-pregna-1,3,5-trien-20-one

HRID 127169Notes

Reaction equation

HRID 127169 reaction equation
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.[O:12]1[C@@H:36]2[C@:13]31[C@H:22]([C@H:23]1[C@:34]([CH3:37])([CH2:35]2)[C@@:26]([OH:38])([C:27](=[O:33])[CH2:28][O:29][C:30](=[O:32])[CH3:31])[CH2:25][CH2:24]1)[CH2:21][CH2:20][C:19]1[C@:14]3([CH3:40])[CH:15]=[CH:16][C:17](=[O:39])[CH:18]=1.N1[CH:46]=[CH:45]C=CC=1.C([CH2:50][C:51]([O-])=[O:52])(C)=C>>[O:12]1[C@@H:36]2[C@:13]31[C@H:22]([C@H:23]1[C@:34]([CH3:37])([CH2:35]2)[C@@:26]([O:38][C:51](=[O:52])[CH3:50])([C:27](=[O:33])[CH2:28][O:29][C:30](=[O:32])[CH3:31])[CH2:25][CH2:24]1)[CH2:21][CH:20]=[C:19]1[C@:14]3([CH3:40])[CH:15]=[CH:16][C:17]([O:39][C:45](=[O:8])[CH3:46])=[CH:18]1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 118762909beta,11beta-Epoxy-17,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetateHCID 18355900Isopropenylacetate

Product 1

HCID 545117149beta,11beta-Epoxy-3,17,21-triacetoxy-pregna-1,3,5-trien-20-one

Procedure

To a solution of 2 g p-toluene sulfonic acid in 100 ml isopropenylacetate was added 20 g of 9β,11β-epoxy-21-acetoxy-17-hydroxypregna-1,4-diene-3,20-dione and the mixture was kept at 80°-85° C. for 2.5 hr with exclusion of moisture. The resulting solution was cooled, neutralized with pyridine (3 ml) and evaporated under high vacuum to give crude 9β,11β-epoxy-3,17,21-triacetoxy-pregna-1,3,5-trien-20-one as a hard gum (25 g) which could not be induced to crystallize (λmax 301 nm ε=5400).

Workup

  1. temperatureThe resulting solution was cooled
  2. customevaporated under high vacuum

Sources & evidence

ORD record
ord-f3cb4c4af8d94446bb856e5cfc91bba2
Source dataset
uspto-grants-1981_03
Patent number
US04255331

Reaction notes

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