Reaction #710568

Reaction equation

NH4Cl

N-(4-(2′,4′-difluorobiphenyl-4-ylsulfonamido)cyclohexyl)-2,2,2-trifluoroacetamide

BH3/THF

water

BH3/THF

→

oil

Yield 79.2%

2′,4′-Difluoro-N-(cis-4-(2,2,2-trifluoroethylamino)cyclohexyl)biphenyl-4-sulfonamide

Yield 79.2%

Solvents

THF

Conditions

Workup

1. 1
   Otherthe reaction
2. 2
   Temperaturethe mixture was heated at 50° C. overnight
3. 3
   TemperatureThe mixture was then cooled
4. 4
   workup.DISSOLUTIONto dissolve all the solids
5. 5
   ExtractionThe mixture was then extracted with EtOAc (3×20 mL)
6. 6
   Dryingthe combined extracts were dried over MgSO4
7. 7
   OtherAfter evaporation of the solvents
8. 8
   Otherthe crude material was purified by column chromatography on SiO2 (30% acetone/hexane)

Procedure

A solution of N-(4-(2′,4′-difluorobiphenyl-4-ylsulfonamido)cyclohexyl)-2,2,2-trifluoroacetamide (350 mg, 0.76 mmol) in THF (20 mL) was stirred under argon at room temperature and BH3/THF (1 M, 3.8 mL) was added. The mixture was heated to 50° C. and stirred for 4 hours, after which LCMS analysis indicated the reaction to be proceeding, but significant starting material was present. Further BH3/THF (1 M, 2.5 mL) was added and the mixture was heated at 50° C. overnight. The mixture was then cooled and NH4Cl (sat. aq., 10 mL) was added cautiously, followed by water to dissolve all the solids. The mixture was then extracted with EtOAc (3×20 mL) and the combined extracts were dried over MgSO4. After evaporation of the solvents, the crude material was purified by column chromatography on SiO2 (30% acetone/hexane) affording a viscous pale yellow oil (270 mg, 79%), which LCMS indicated to be only 78% pure and a mixture of diastereomers.

Source