17-Cyclopropyloxy-4-nitroandrost-4-en-3-one → 4-Amino-17-cyclopropyloxyandrost-4-en-3-one

HRID 1604106Notes

Reaction equation

HRID 1604106 reaction equation
[CH:1]1([O:4][CH: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 5394442517-Cyclopropyloxy-4-nitroandrost-4-en-3-one

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 17-cyclopropyloxy-4-nitroandrost-4-en-3-one (1.0 g, 2.71 mM) in acetic acid (10 mL) is treated with zinc dust (1.0 g). The combination 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 further 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. extractionfurther extracted with ether
  8. dry with materialThe combined organic layers are then dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9aeea94ee50f438d8fc130119f6388c4
Source dataset
uspto-grants-1999_11
Patent number
US05990328

Reaction notes

Loading…