Sodium borohydride → 2Alpha,3alpha-epoxy-16beta-(1-pyrrolidinyl)-5alpha-androstan-17beta-OL

HRID 232758

Reaction equation

HRID 232758 reaction equation
[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

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 16063837(2αlpha,3αlpha,5αlpha,16beta)-2,3-Epoxy-16-(1-pyrrolidinyl)androstan-17-one

Product 1

HCID 160638722Alpha,3alpha-epoxy-16beta-(1-pyrrolidinyl)-5alpha-androstan-17beta-OL

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0d678ac59c064668847b731576bd4390
Source dataset
uspto-grants-1997_01
Patent number
US05591735

Linked notes

Loading…