Dehydroepiandrosterone → HCID 15009206, compound

HRID 1461549Notes

Reaction equation

HRID 1461549 reaction equation
[CH3:1][C@@:2]12[C:10](=O)[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[CH:22]1([NH2:25])[CH2:24][CH2:23]1>CO>[CH:22]1([N:25]=[C:10]2[CH2:9][CH2:8][C@H:7]3[C@H:6]4[C@H:5]([CH2:4][CH2:3][C@:2]23[CH3:1])[C@:15]2([CH3:21])[C:14]([CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16]2)=[CH:13][CH2:12]4)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 5881DehydroepiandrosteroneHCID 69828Cyclopropylamine

Product 1

HCID 15009206HCID 15009206, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 21 g of dehydroepiandrosterone in a mixture of 175 ml of cyclopropylamine and 150 ml of methanol was added 5 g of molecular sieves The reaction mixture was refluxed for 48 hours, cooled to room temperature, and filtered through magnesium sulfate. The magnesium sulfate was washed with ethyl acetate and the solvent was removed from the combined filtrates under reduced pressure to give 17-(cyclopropylimino)androst-5-en-3β-ol melting at about 187° C.

Workup

  1. additionwas added 5 g of molecular sieves The reaction mixture
  2. temperaturewas refluxed for 48 hours
  3. filtrationfiltered through magnesium sulfate
  4. washThe magnesium sulfate was washed with ethyl acetate
  5. customthe solvent was removed from the combined filtrates under reduced pressure

Sources & evidence

ORD record
ord-5b114bd3855e44b78b61414e3cdf11b4
Source dataset
uspto-grants-1991_12
Patent number
US05075464

Reaction notes

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