Lithium hydroxide, monohydrate → HCID 67857076, compound

HRID 1587036Notes

Reaction equation

HRID 1587036 reaction equation
[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([CH2:21][C@H:22]([O:23]C(=O)C)[C@:5]12[CH3:6])[C@:18]1([CH3:19])[C@@H:13]([CH2:14][C@H:15]([O:27]C(=O)C)[CH2:16][CH2:17]1)[CH2:12][C@H:11]3[O:31]C(=O)C)(=[O:3])[CH3:2].O.[OH-].[Li+]>CO.O.O1CCCC1>[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:20]([CH2:21][C@H:22]([OH:23])[C@:5]12[CH3:6])[C@:18]1([CH3:19])[C@@H:13]([CH2:14][C@H:15]([OH:27])[CH2:16][CH2:17]1)[CH2:12][C@H:11]3[OH:31])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22295271HCID 22295271, compound

Product 1

HCID 67857076HCID 67857076, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 17β-acetyl-3α,7α,12α-triacetoxy-5β-androstane (9.48 g) and lithium hydroxide monohydrate (4.0 g) in methanol (20 ml), water (20 ml) and tetrahydrofuran (20 ml) is stirred at room temperature for about 19 hours, concentrated in vacuo, diluted with ethyl acetate and washed with brine. The organic solution is dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude is purified by flash chromatography in ethyl acetate to give the desired product.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic solution is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude is purified by flash chromatography in ethyl acetate

Sources & evidence

ORD record
ord-058a52e835ad4632bc57fc69142b6c83
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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