Acetic Acid → 19-Hydroxytestosterone

HRID 597356

반응식

HRID 597356 반응식
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[CH2:15][CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:21])[CH2:5][CH2:4]2.[BH4-].[K+].O.C(O)(=[O:27])C>C(O)C>[OH:27][C@H:15]1[CH2:14][CH2:13][C@H:12]2[C@H:11]3[C@H:20]([CH2:19][CH2:18][C@:16]12[CH3:17])[C@:3]1([CH2:2][OH:1])[C:8](=[CH:7][C:6](=[O:21])[CH2:5][CH2:4]1)[CH2:9][CH2:10]3

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 4192641Potassium borohydride3회HCID 2280225719-Hydroxy-4-androsten-3-one

생성물 1

HCID 15096819-Hydroxytestosterone

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

A solution of 150 g of 19-hydroxyandrost-4-en-3-one in 6 liters of ethanol is cooled in an ice bath. To this cold solution is added 13.5 g of potassium borohydride, and the reaction mixture is stirred for two hours at about 0° C after which a second 13.5 g or potassium borohydride is added. Two hours later a third 13.5 g portion of potassium borohydride is added to the reaction mixture which is stirred for an additional one hour then poured into 11 liters of water to which 70 ml of acetic acid is added. The ethanol is distilled off under reduced pressure and the aqueous residue cooled to 0° C. The solid which separates is filtered off, dried and dissolved in 25 liters of hot chloroform after which the temperature is adjusted to 25° C. To the chloroform solution is added 250 g of manganese dioxide, and the mixture is stirred for two hours then filtered and the solvents removed under reduced pressure. The solid residue is recrystallized from acetonitrile to give 17β,19-dihydroxyandrost-4-en-3-one. M.P. 205°-207° C.

후처리

  1. additionis added
  2. additionis added
  3. distillationThe ethanol is distilled off under reduced pressure
  4. filtrationThe solid which separates is filtered off
  5. customdried
  6. dissolutiondissolved in 25 liters of hot chloroform after which the temperature
  7. customis adjusted to 25° C
  8. additionTo the chloroform solution is added 250 g of manganese dioxide
  9. stirringthe mixture is stirred for two hours
  10. filtrationthen filtered
  11. customthe solvents removed under reduced pressure
  12. customThe solid residue is recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-8c0e81e8c02f41e9bd8dae847156fa4b
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04013762

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