Water → HCID 66582855, compound

HRID 1972433Notes

Reaction equation

HRID 1972433 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([C:23]([F:26])([F:25])[F:24])=[CH2:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])=[O:7].N1C=CC=CC=1.[O-:33]S([O-])=O.[Na+].[Na+].[OH2:39]>[Os](=O)(=O)(=O)=O>[F:24][C:23]([F:26])([F:25])[C:21]([C:18]1[CH:17]=[CH:16][C:15]([N:12]2[CH2:11][CH2:10][N:9]([S:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)(=[O:7])=[O:8])[CH2:14][CH2:13]2)=[CH:20][CH:19]=1)([OH:33])[CH2:22][OH:39]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24437Sodium SulfiteHCID 66582483HCID 66582483, compound

Product 1

HCID 66582855HCID 66582855, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

Osmium tetroxide (2.4 mL, 4 wt % solution in water, 0.40 mmol) was added to a stirring solution of 1-(2-thiophenylsulfonyl)-4-(4-(1-(trifluoromethyl)ethenyl)phenyl)piperazine (0.16 g, 0.40 mmol) and pyridine (4.0 mL) at room temperature. After 40 min, water (4.0 mL) and Na2SO3 (1.5 g, 12 mmol) were added sequentially, the mixture was partitioned between water (10 mL) and chloroform (25 mL). The layers were separated and the aqueous material was washed with chloroform (2×10 mL). The combined organic material was dried (Na2SO4) and purified via column chromatography (10 g of silica, 1% MeOH in CH2Cl2). The purified residue was partitioned between water (20 mL) and tert-butanol (20 mL). To this was added sodium sulfite (2.0 g), potassium carbonate (2.0 g), and methanesulfonamide (0.20 g) at room temperature. After 6 h, the reaction mixture was partitioned between EtOAc (50 mL) and saturated aqueous sodium bicarbonate (25 mL) and the layers were separated. The organic material was washed sequentially with saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL), dried (MgSO4), and purified via column chromatography on silica gel (10 g of silica, 1% MeOH in CH2Cl2) to yield 3,3,3-trifluoro-2-(4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,2-propanediol as a mixture of enantiomers (0.088 g).

Workup

  1. customthe mixture was partitioned between water (10 mL) and chloroform (25 mL)
  2. customThe layers were separated
  3. washthe aqueous material was washed with chloroform (2×10 mL)
  4. dry with materialThe combined organic material was dried (Na2SO4)
  5. custompurified via column chromatography (10 g of silica, 1% MeOH in CH2Cl2)
  6. customThe purified residue was partitioned between water (20 mL) and tert-butanol (20 mL)
  7. additionTo this was added sodium sulfite (2.0 g), potassium carbonate (2.0 g), and methanesulfonamide (0.20 g) at room temperature
  8. waitAfter 6 h
  9. customthe reaction mixture was partitioned between EtOAc (50 mL) and saturated aqueous sodium bicarbonate (25 mL)
  10. customthe layers were separated
  11. washThe organic material was washed sequentially with saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL)
  12. dry with materialdried (MgSO4)
  13. custompurified via column chromatography on silica gel (10 g of silica, 1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4418ef1ba59249319b98cee575752998
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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