HCID 10981608, compound → 4-Amino-17-cyclopropyloxyandrost-4-en-3-one

HRID 375515Notes

Reaction equation

HRID 375515 reaction equation
[CH:1]1([O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14](=[C:15]([N+:25]([O-])=O)[C:16](=[O:24])[CH2:17][CH2:18]2)[CH2:13][CH2:12]4)[CH2:3][CH2:2]1>C(O)(=O)C.[Zn]>[NH2:25][C:15]1[C:16](=[O:24])[CH2:17][CH2:18][C@@:19]2([CH3:20])[C:14]=1[CH2:13][CH2:12][C@@H:11]1[C@@H:21]2[CH2:22][CH2:23][C@@:6]2([CH3:7])[C@H:8]1[CH2:9][CH2:10][CH:5]2[O:4][CH:1]1[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 10981608HCID 10981608, compound

Product 1

HCID 153410014-Amino-17-cyclopropyloxyandrost-4-en-3-oneYield 64.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 17β-cyclopropyloxy-4-nitroandrost-4-en-3-one (1.0 g, 2.71 mM), either prepared above or by other known techniques, in acetic acid (10 ml) is treated with zinc dust (1.0 g). The combination (mixture) is vigorously stirred for 1.5 hours at room temperature. The zinc salts are removed by filtration and washed with ethyl acetate. The combined filtrate and wash are combined and concentrated to a yellow solid which is then redissolved in ethyl acetate and extracted three times with 1M hydrochloric acid (150 ml), The combined acid extracts are neutralized with sodium hydroxide (pH 14) and extracted with ether. The combined organic layers are then dried over sodium sulfate and concentrated to give 4-amino-17-cyclopropyloxyandrost-4-en-3-one (0.59 g), m.p. 100°-102° C. (aqueous methanol).

Workup

  1. customThe zinc salts are removed by filtration
  2. washwashed with ethyl acetate
  3. washThe combined filtrate and wash
  4. concentrationconcentrated to a yellow solid which
  5. dissolutionis then redissolved in ethyl acetate
  6. extractionextracted three times with 1M hydrochloric acid (150 ml)
  7. extractionextracted with ether
  8. dry with materialThe combined organic layers are then dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-727e6f0c170f4a18b10b7b29f3acfb56
Source dataset
uspto-grants-1996_01
Patent number
US05486511

Reaction notes

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