Sodium Hydroxide → 92472-37-2

HRID 840173Notes

Reaction equation

HRID 840173 reaction equation
C([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14]([N:15]([CH3:25])[C:16](=[O:24])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)(=O)C.[OH-].[Na+]>C(O)C>[OH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14]([N:15]([CH3:25])[C:16](=[O:24])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15543050HCID 15543050, compound

Product 1

HCID 24547192472-37-2Yield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17β-Acetoxy-4-methyl-4-aza-androst-5(6)-en-3-one (3.373 g, 9.763 mmol) is dissolved in ethanol (50 mL). Concentrated sodium hydroxide (6M, 25.0 mL) is added and the reaction is stirred at room temperature for 4 ½ hours. The reaction is partitioned between brine (10.0 mL) and EtOAc (100 mL). The layers are separated and the organic layer washed with brine (2×100 mL), saturated NH4Cl (100 mL), dried over MgSO4, filtered and evaporated to give a crude reaction product as a yellow solid. This is purified by dissolving in methanol and evaporating until the formation of large crystals is seen. The crystals are washed in acetone and dried overnight at reduced pressure (0.3 mm Hg) to give 17β-hydroxy-4-methyl-4-aza-androst-5(6)-en-3-one of very good purity (1.8119 g, 5.9712 mmol). Yield: 61%. m.p. 188° C.-192° C.

Workup

  1. customThe reaction is partitioned between brine (10.0 mL) and EtOAc (100 mL)
  2. customThe layers are separated
  3. washthe organic layer washed with brine (2×100 mL), saturated NH4Cl (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude
  8. customreaction product as a yellow solid
  9. customThis is purified
  10. dissolutionby dissolving in methanol
  11. customevaporating until the formation of large crystals
  12. washThe crystals are washed in acetone
  13. customdried overnight at reduced pressure (0.3 mm Hg)

Sources & evidence

ORD record
ord-b502e30d4d6b4cf895c8488db46a3519
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

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