Sodium Hydroxide → HCID 20683881, compound

HRID 1595964Notes

Reaction equation

HRID 1595964 reaction equation
C([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH:18]=[CH:17][C:16]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[CH:15][C:14]=1[CH2:13][C@H:12]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][CH3:36])(=O)C.[OH-].[Na+]>CO.C(OCC)(=O)C>[CH3:36][NH:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][C@@H:12]1[CH2:13][C:14]2[CH:15]=[C:16]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH:17]=[CH:18][C:19]=2[C@@H:20]2[C@@H:11]1[C@H:8]1[C@@:6]([CH2:22][CH2:21]2)([CH3:7])[C@@H:5]([OH:4])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22941792HCID 22941792, compound

Product 1

HCID 20683881HCID 20683881, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 307 mg of 17β-acetoxy-7α-{5-methylaminopentyl}-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene (Example 1h) in 6 ml of methanol is stirred with 1.5 ml of sodium hydroxide solution for 4 hours at room temperature. Then, it is diluted with ethyl acetate, washed with water, dried on sodium sulfate and concentrated by evaporation in a vacuum. 285 mg of 7α-{5-methylaminopentyl}-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-trien-17β-ol is obtained.

Workup

  1. washwashed with water
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-75a88b1c69f5462c97c9e1c6b7578c1d
Source dataset
uspto-grants-2001_09
Patent number
US06288051B1

Reaction notes

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