Acetic Anhydride → 21-Acetoxy-3,3-ethylenedioxy-20-nitropregna-5,16-dien-9alpha-ol

HRID 1613969Notes

Reaction equation

HRID 1613969 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]1[CH2:37][O:36][C:10]2([CH2:32][CH2:31][C@@:30]3([CH3:33])[C:12](=[CH:13][CH2:14][C@@H:15]4[C@:29]3([OH:34])[CH2:28][CH2:27][C@@:26]3([CH3:35])[C@H:16]4[CH2:17][CH:18]=[C:19]3[CH:20]([N+:23]([O-:25])=[O:24])[CH2:21][OH:22])[CH2:11]2)[O:9]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([O:22][CH2:21][CH:20]([N+:23]([O-:25])=[O:24])[C:19]1[C@:26]2([CH3:35])[C@H:16]([C@H:15]3[C@:29]([OH:34])([CH2:28][CH2:27]2)[C@:30]2([CH3:33])[C:12]([CH2:11][C:10]4([O:9][CH2:8][CH2:37][O:36]4)[CH2:32][CH2:31]2)=[CH:13][CH2:14]3)[CH2:17][CH:18]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 542775113,3-Ethylenedioxy-20-nitropregna-5,16-diene-9alpha,21-diol

Product 1

HCID 5712100521-Acetoxy-3,3-ethylenedioxy-20-nitropregna-5,16-dien-9alpha-ol

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (1.5 ml) was added to a stirred suspension of 3,3-ethylenedioxy-20-nitropregna-5,16-diene-9α,21-diol (1.00 g of diastereomer II, prepared according to example 2), and 4-dimethylaminopyridine (100 mg) in methylene chloride (10 ml) to give a clear solution. The reaction mixture was stirred for an additional 30 minutes and concentrated under reduced pressure. The residue was dissolved in methylene chloride and filtered over a silica gel column. The filtrate was evaporated under reduced pressure to afford a white solid which was dried under reduced pressure at 50° C.

Workup

  1. customto give a clear solution
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. filtrationfiltered over a silica gel column
  5. customThe filtrate was evaporated under reduced pressure
  6. customto afford a white solid which
  7. customwas dried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-bfd665e02d7842369a83420e9194bc70
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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