Lithium borohydride → 4-Fluoro-3-methyl-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzenesulfonamide

HRID 1987583Notes

Reaction equation

HRID 1987583 reaction equation
C([O:3][C:4](=O)[CH:5]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([CH3:26])[CH:20]=1)(=[O:18])=[O:17])[CH:6]([C:11]([F:14])([F:13])[F:12])[C:7]([F:10])([F:9])[F:8])C.[Li+].[BH4-]>C1COCC1>[F:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([NH:15][CH:5]([CH2:4][OH:3])[CH:6]([C:7]([F:8])([F:9])[F:10])[C:11]([F:13])([F:12])[F:14])(=[O:17])=[O:18])=[CH:20][C:21]=1[CH3:26]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 866160074,4,4-Trifluoro-2-(4-fluoro-3-methyl-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester

Product 1

HCID 247657444-Fluoro-3-methyl-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzenesulfonamideYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4,4,4-trifluoro-2-(4-fluoro-3-methyl-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester (29 mg, 0.068 mmol) in anhydrous THF (3 mL) at 0° C. was added 2M LiBH4 (50 μL). The solution was allowed to warm to 25° C. After 18 h, the solution was quenched with 1N HCl and the solvent removed in vacuo. The remaining aqueous phase was transferred to a separatory funnel with distilled water (100 mL) and extracted with EtOAc (100 mL). The organic layer was removed and the aqueous phase extracted with EtOAc (100 mL×2). The organic extracts were combined, washed with brine (100 mL), dried (MgSO4), filtered and evaporated to give a white solid (21 mg). This material was purified by Gilson RP-HPLC (column YMC Combiprep 50×20 mm, gradient 10-100% CH3CN: H2O) to afford a white solid (14 mg, 54%). Mass Spectrum (−ESI): 382 [M−H]−.

Workup

  1. customthe solution was quenched with 1N HCl
  2. customthe solvent removed in vacuo
  3. customThe remaining aqueous phase was transferred to a separatory funnel with distilled water (100 mL)
  4. extractionextracted with EtOAc (100 mL)
  5. customThe organic layer was removed
  6. extractionthe aqueous phase extracted with EtOAc (100 mL×2)
  7. washwashed with brine (100 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-7284cc6e9b4e48efa2d2594e048dd3c6
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

Loading…