Acetone → 16-Azido-3-methoxyestra-1(10),2,4-trien-17-one

HRID 1050287Notes

Reaction equation

HRID 1050287 reaction equation
[N:1]([C@@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C@H:5]1[OH:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)=[N+:2]=[N-:3].CC(C)=O.C(O)(C)C>S(=O)(=O)(O)O.[O-2].[O-2].[O-2].[Cr+6]>[N:1]([C@@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C:5]1=[O:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 180AcetoneHCID 3776IsopropanolHCID 21723401HCID 21723401, compound

Product 1

HCID 16265816-Azido-3-methoxyestra-1(10),2,4-trien-17-one

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 20 g 16α-azido-3-methoxy-estra-1,3,5(10)-triene-17β-ol in 11 acetone, 40 ml of 8 N chromium trioxide solution in conc. sulfuric acid is added dropwise at 0° C. and under stirring. After 2 h, 2 ml isopropanol are added and the reaction product is precipitated in crystalline form by dropwise addition of water. The product is filtered off, washed with water, dried and recrystallized from acetone/water. Yield: 16 g (81%), F=118-122° C.; [α]D+405°. IR: 1747 cm (CO), 2095 (N3).

Workup

  1. customthe reaction product is precipitated in crystalline form by dropwise addition of water
  2. filtrationThe product is filtered off
  3. washwashed with water
  4. customdried
  5. customrecrystallized from acetone/water
  6. customYield: 16 g (81%), F=118-122° C.

Sources & evidence

ORD record
ord-47b6e540f34d4cbba60c0197cc9738c5
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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