Sodium borohydride → HCID 86735970, compound

HRID 2420238Notes

Reaction equation

HRID 2420238 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[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1)[CH2:10]2)[CH2:7][CH2:6]3.[BH4-].[Na+]>C(Cl)Cl.CO>[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][N:25]([CH3:28])[CH2:26][CH2:27]1)[CH2:10]2)[CH2:7][CH2:6]3

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86735971HCID 86735971, compound

Product 1

HCID 86735970HCID 86735970, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

15 g (0.038 mole) of 2α,3α-epoxy-17-oxo-16β-N-Methyl-piperazino-5α-androstane (Example 9) are dissolved in the mixture of 45 ml of methylene chloride and 120 ml of methanol, whereafter 12 g (0.31 mole) of sodium borohydride are added at a temperature of below 30° C. When the addition is complete, the product of the reduction is crystallized. The crystalline solution is stirred vigorously for 12 hours, whereafter the solvent is distilled at reduced pressure at a temperature of below 40° C. The residue is triturated with water, the crystallized product is filtered, dissolved in chloroform and washed with 5% aqueous sodium hydroxide solution and with water until pH = 7. The layers are separated. The chloroform layer is dried on sodium sulfate, filtered and the filtrate is evaporated to dryness. The residue is recrystallized from acetonitrile. Yield: 11.7 g (77.2%) of 2α,3α-epoxy-17β-N-methyl-piperazino-5α-androstane; m.p. 149°-153° C; [α]D25 = +27.1° (c = 1 in chloroform).

Workup

  1. additionare added at a temperature of below 30° C
  2. additionWhen the addition
  3. customthe product of the reduction is crystallized
  4. distillationis distilled at reduced pressure at a temperature of below 40° C
  5. customThe residue is triturated with water
  6. filtrationthe crystallized product is filtered
  7. dissolutiondissolved in chloroform
  8. washwashed with 5% aqueous sodium hydroxide solution and with water until pH = 7
  9. customThe layers are separated
  10. dry with materialThe chloroform layer is dried on sodium sulfate
  11. filtrationfiltered
  12. customthe filtrate is evaporated to dryness
  13. customThe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-cb04d0ac095244919b41f9cfbff69c44
Source dataset
uspto-grants-1978_08
Patent number
US04110326

Reaction notes

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