Bazedoxifene Acetate → Bazedoxifene

HRID 1503317

Reaction equation

HRID 1503317 reaction equation
[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]([OH:35])[CH:6]=[CH:7][C:8]=2[N:9]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:23][CH:24]=2)[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1.CC(O)=O>CS(C)=O>[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]([OH:35])[CH:6]=[CH:7][C:8]=2[N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:21][CH:20]=2)[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1

Participants

3

Reactant 1

HCID 154256Bazedoxifene Acetate

Product 1

HCID 154257BazedoxifeneYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

Bazedoxifene acetate (3 g) and dimethylsulfoxide (15 mL) are mixed and heated to 60-70° C. to produce a clear solution, followed by cooling to room temperature and filtration to make it particle free. To the filtrate, toluene (150 mL), 10% aqueous sodium carbonate solution (5 mL) and water (75 mL) are added and the mixture is stirred at room temperature for solid formation. The solid so formed is collected by filtration, washed with toluene (6 mL), water (6 mL) and dried under vacuum below 80° C. for about 7 hours to afford 2.5 g of crystalline bazedoxifene free base Form A.

Workup

  1. customto produce a clear solution
  2. temperatureby cooling to room temperature
  3. filtrationfiltration
  4. additionTo the filtrate, toluene (150 mL), 10% aqueous sodium carbonate solution (5 mL) and water (75 mL) are added
  5. customThe solid so formed
  6. filtrationis collected by filtration
  7. washwashed with toluene (6 mL), water (6 mL)
  8. customdried under vacuum below 80° C. for about 7 hours

Sources & evidence

ORD record
ord-0616b5f881544275bb673f0cc2cd4451
Source dataset
uspto-grants-2015_12
Patent number
US09212172B2

Linked notes

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