Dimethylformamide → HCID 86733303, compound

HRID 1606368Notes

Reaction equation

HRID 1606368 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:20]([CH3:22])([CH2:21][C@@H:2]12)[C@@H:19]1[C@H:8]([C@H:9]2[C@:16]([CH3:24])([CH2:17][C:18]1=[O:23])[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.[N-:25]=[N+:26]=[N-:27].[Na+].CN(C)C=O>O>[N:25]([C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4][C@@H:3]1[OH:1])=[N+:26]=[N-:27]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium Azide2×HCID 86733130HCID 86733130, compound

Product 1

HCID 86733303HCID 86733303, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2α,3α-epoxy-5α-pregnane-11,20-dione (1 g) was added to a mixture of sodium azide (1g), boric acid (1g) and dimethylformamide (20 ml) and the mixture refluxed for 5 hours. The mixture was cooled, poured into water and the resulting emulsion extracted into methylene chloride (2 × 150 ml.). The organic extracts were washed with water (2 × 300 ml.) dried over anhydrous sodium sulphate and evaporated to a red oil which was purified by preparative T.L.C. using ethyl acetate/petrol (1/1), the main band giving 2β-azido-3α-hydroxy-5α-pregnane-11,20-dione (580 mg) as a foam.

Workup

  1. temperaturethe mixture refluxed for 5 hours
  2. temperatureThe mixture was cooled
  3. extractionthe resulting emulsion extracted into methylene chloride (2 × 150 ml.)
  4. washThe organic extracts were washed with water (2 × 300 ml.)
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated to a red oil which
  7. customwas purified by preparative T.L.C

Sources & evidence

ORD record
ord-305839f388964d36b1efc605d75fbcd1
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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