1,3-Propanedithiol → HCID 70395931, compound

HRID 1905010Notes

Reaction equation

HRID 1905010 reaction equation
[N:1]([C@@H:4]1[C:21]2[C@:16]([CH3:24])([CH:17]3[CH2:23][C@@H:18]3[C:19](=[O:22])[CH:20]=2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:25])[CH2:9][CH2:8]3)[CH2:5]1)=[N+]=[N-].C(S)CCS.C(N(CC)CC)C>CO>[NH2:1][C@@H:4]1[C:21]2[C@:16]([CH3:24])([CH:17]3[CH2:23][C@@H:18]3[C:19](=[O:22])[CH:20]=2)[C@@H:15]2[C@H:6]([C@H:7]3[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C:10](=[O:25])[CH2:9][CH2:8]3)[CH2:5]1

Participants

5

Reactant 3

HCID 80131,3-PropanedithiolHCID 8471TriethylamineHCID 131715974HCID 131715974, compound

Product 1

HCID 70395931HCID 70395931, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6α-azido-1,2β-methylenandrost-4-ene-3,17-dione (1695 mg, 5 mmol), 1,3-propanedithiol (0.25 ml, 2.5 mmol), triethylamine (0.35 ml, 2.5 mmol) and methanol (2.5 ml) is stirred for 6 hours at room temperature. Then the reaction mixture is evaporated in vacuo to dryness. The residue is taken up in ether, the etheral solution washed with water, dried and evaporated in vacuo. Column chromatography of the residue over silica gel affords the pure 6α-amino-1,2β-methylenandrost-4-ene-3,17-dione (1000 mg, 64%).

Workup

  1. customThen the reaction mixture is evaporated in vacuo to dryness
  2. washthe etheral solution washed with water
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-0c20d4ee4f7f446d9d0df7816f1aec37
Source dataset
uspto-grants-1989_06
Patent number
US04840943

Reaction notes

Loading…