Acetone → Bazedoxifene

HRID 1503315Notes

Reaction equation

HRID 1503315 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:15][CH:14]=2)[C:3]=1[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1.Cl.C(OCC)(=O)C.CC(C)=O.[OH-].[Na+]>O>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[N:4]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:17][CH:18]=2)[C:3]=1[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 9936012Bazedoxifene HCl

Product 1

HCID 154257BazedoxifeneYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bazedoxifene hydrochloride (2 g), ethyl acetate (20 mL) and acetone (30 mL) are mixed. To the mixture, 10% aqueous sodium hydroxide solution (5 mL) is drop-wise added followed by addition of water (120 mL) and stirring is continued at room temperature for solid formation. The solid so formed is collected by filtration, washed with water (20 mL) and dried under vacuum below 75° C. for about 6-8 hours to afford 1.8 g of crystalline bazedoxifene free base Form A.

Workup

  1. customis continued at room temperature for solid formation
  2. customThe solid so formed
  3. filtrationis collected by filtration
  4. washwashed with water (20 mL)
  5. customdried under vacuum below 75° C. for about 6-8 hours

Sources & evidence

ORD record
ord-c993c31b0a854e1194bacef35ddb4a8d
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Reaction notes

Loading…