Methanol → Dehydroepiandrosterone

HRID 531214Notes

Reaction equation

HRID 531214 reaction equation
C(Cl)Cl.C[C@@:5]12[C@H:14]3[CH2:15][CH2:16][C@:17]4(C)[C:21]([C:22]5[CH:23]=[CH:24]C=NC=5)=C[CH2:19][C@H:18]4[C@@H:13]3[CH2:12][CH:11]=[C:10]1[CH2:9][C@@H:8]([OH:29])[CH2:7][CH2:6]2.C[OH:31]>>[CH3:9][C@@:10]12[C:8](=[O:29])[CH2:7][CH2:6][C@H:5]1[C@@H:14]1[CH2:15][CH:16]=[C:17]3[CH2:21][C@@H:22]([OH:31])[CH2:23][CH2:24][C@:18]3([CH3:19])[C@H:13]1[CH2:12][CH2:11]2

Participants

4

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 132971Abiraterone

Product 1

HCID 5881Dehydroepiandrosterone

Conditions

Temperature
42.5 °C

Procedure

34.8 ml of CH2Cl2 and 26.1 ml of methanol were added to 8.7 g (24.9 mmol) of crude stage 3 (abiraterone). The mixture was heated to 40-45° C. (reflux), to have a solution. The CH2Cl2 was then removed by distillation at atmospheric pressure. The mixture was cooled to 0-5° C., and then maintained 1 hour at 0-5° C. The suspension was filtered (fast filtration) and the cake was washed twice with 4.4 ml of methanol cooled to 0-5° C. The wet solid was dried at 40-45° C. under vacuum for 5 hours to give 7.2 g (yield of purification 82.8%) of pure stage 3 (abiraterone). The overall yield from DHEA was around 50%.

Workup

  1. temperature(reflux)
  2. customThe CH2Cl2 was then removed by distillation at atmospheric pressure
  3. temperatureThe mixture was cooled to 0-5° C.
  4. temperaturemaintained 1 hour at 0-5° C
  5. filtrationThe suspension was filtered
  6. filtration(fast filtration)
  7. washthe cake was washed twice with 4.4 ml of methanol
  8. temperaturecooled to 0-5° C
  9. customThe wet solid was dried at 40-45° C. under vacuum for 5 hours
  10. customto give
  11. custom7.2 g (yield of purification 82.8%) of pure stage 3 (abiraterone)

Sources & evidence

ORD record
ord-a84496c86d7842c290a341f5b936b386
Source dataset
uspto-grants-2016_05
Patent number
US09353145B2

Reaction notes

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