Cyclopropylamine → HCID 15085906, compound

HRID 1089421Notes

Reaction equation

HRID 1089421 reaction equation
[F:1][C:2]1([F:29])[C@@H:19]([O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH2:18][CH2:17][C@@:16]2([CH3:27])[C:3]1=[CH:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=O.[CH:30]1([NH2:33])[CH2:32][CH2:31]1>CO>[CH:30]1([N:33]=[C:10]2[CH2:9][CH2:8][C@H:7]3[C@H:6]4[C@H:15]([CH2:14][CH2:13][C@:11]23[CH3:12])[C@:16]2([CH3:27])[C:3]([C:2]([F:1])([F:29])[C@@H:19]([O:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[CH2:18][CH2:17]2)=[CH:4][CH2:5]4)[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 15085905HCID 15085905, compound

Product 1

HCID 15085906HCID 15085906, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 21 g of 4,4-difluoro-3β-(2-tetrahydropyranyloxy)androst-5-en-17-one in a mixture of 175 ml of cyclopropylamine and 150 ml of methanol there is added 5 g of molecular sieves. The reaction mixture is refluxed for 48 hours, cooled to room temperature, and filtered through magnesium sulfate. The magnesium sulfate is washed with ethyl acetate and the solvent is removed from the combined filtrates under reduced pressure to give 17-(cyclopropylimino)-4,4-difluoro-3β-(2-tetrahydropyranyloxy)androst-5-ene.

Workup

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

Sources & evidence

ORD record
ord-841049cc2607469f958491043ce6b6b3
Source dataset
uspto-grants-1990_10
Patent number
US04966898

Reaction notes

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