硼氢化钠 → (2α,3α,5α，16β,17β)-2,3-环氧-16-(1-吡咯烷)-雄甾烷-17-醇

HRID 232758

反应方程式

HRID 232758 反应方程式
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C:12](=[O:21])[C@@H:11]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:10]2)[CH2:7][CH2:6]3.[BH4-].[Na+]>CO.C(Cl)Cl>[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C@@H:12]([OH:21])[C@@H:11]([N:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1)[CH2:10]2)[CH2:7][CH2:6]3

参与物

5

反应物 2

HCID 4311764硼氢化钠HCID 16063837(2αlpha,3αlpha,5αlpha,16beta)-2,3-Epoxy-16-(1-pyrrolidinyl)androstan-17-one

产物 1

HCID 16063872(2α,3α,5α，16β,17β)-2,3-环氧-16-(1-吡咯烷)-雄甾烷-17-醇

试剂、催化剂与溶剂 2

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 6344二氯甲烷溶剂

实验过程

After dissolving 39.2 g of 2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstan-17-one in a mixture of 392 ml of methanol and 56 ml of methylene chloride. 14.7 g Sodium borohydride are portionwise added while stirring and introducing nitrogen at such a rate that the temperature reaches room temperature as a maximum. The solution containing a precipitate is left to stand for 12 hours, then methylene chloride is evaporated, and the residue is diluted with water. The precipitate is filtered, thoroughly washed with water, dried and recrystallized from methanol to obtain the title product in a yield of 33.3 g (89.5%), m.p.: 167°-169° C.

后处理

  1. additionintroducing nitrogen at such a rate that the temperature
  2. customreaches room temperature as a maximum
  3. additionThe solution containing a precipitate
  4. waitis left
  5. custommethylene chloride is evaporated
  6. additionthe residue is diluted with water
  7. filtrationThe precipitate is filtered
  8. washthoroughly washed with water
  9. customdried
  10. customrecrystallized from methanol

来源与证据

ORD记录
ord-0d678ac59c064668847b731576bd4390
来源数据集
uspto-grants-1997_01
专利号
US05591735

关联笔记

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