3beta-Acetoxy-14beta-hydroxy-5beta-pregnane-21-nitrile → HCID 10782753, compound

HRID 1080637Notes

Reaction equation

HRID 1080637 reaction equation
C([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@:11]3([OH:27])[CH2:12][CH2:13][C@@H:14]2[CH2:15][C:16]#[N:17])[CH2:6]1)(=O)C.P([O-])(O)(O)=O.[Na+]>CO.O1CCCC1.[OH-].[Na+]>[OH:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@:11]3([OH:27])[CH2:12][CH2:13][C@@H:14]2[CH2:15][C:16]#[N:17])[CH2:6]1

Participants

6

Reactant 2

HCID 107855783beta-Acetoxy-14beta-hydroxy-5beta-pregnane-21-nitrileHCID 23672064Monosodium phosphate

Product 1

HCID 10782753HCID 10782753, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 11.18 g of 3β-acetoxy-14β-hydroxy-5β-pregnane-21-nitrile in 260 ml of methanol, 260 ml of tetrahydrofuran and 143 ml of 1N NaOH was stirred at room temperature for 20 hrs. The mixture was then neutralized with sodium dihydrogenphosphate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to dryness under reduced pressure to give 8.55 g of 3β,14β-dihydroxy-5β-pregnane-21-nitrile.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3f7386e5c438412fa3990b8e10a67a8d
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

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