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

HRID 1290315Notes

Reaction equation

HRID 1290315 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). IR 3354, 1662, 1620, 1581 cm-1MS(CI) 344(100%, M+1) 1H-NMR 0.37-0.61(4H, m, 2 x cyclopropyl CH2), 0.79(3H, s, C18 -Me), 1.16(s, Ci9 -Me), 3.25-3.33(m, cyclopropyl-CHO), 3.44(t, C17 -H).

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-06a973367a04400f9ca789289cfd220d
Source dataset
uspto-grants-1998_05
Patent number
US05750744

Reaction notes

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