Water → HCID 178527588, compound

HRID 69576Notes

Reaction equation

HRID 69576 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]2[CH2:24][CH2:23][CH:22]([NH:25][C:26](=O)[C:27]([F:30])([F:29])[F:28])[CH2:21][CH2:20]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1.B.C1COCC1.[NH4+].[Cl-].O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@H:19]2[CH2:20][CH2:21][C@@H:22]([NH:25][CH2:26][C:27]([F:29])([F:30])[F:28])[CH2:23][CH2:24]2)(=[O:16])=[O:17])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2723981Borane;tetrahydrofuran2×HCID 58344297HCID 58344297, compound

Product 1

HCID 178527588HCID 178527588, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

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.

Workup

  1. customthe reaction
  2. temperaturethe mixture was heated at 50° C. overnight
  3. temperatureThe mixture was then cooled
  4. dissolutionto dissolve all the solids
  5. extractionThe mixture was then extracted with EtOAc (3×20 mL)
  6. dry with materialthe combined extracts were dried over MgSO4
  7. customAfter evaporation of the solvents
  8. customthe crude material was purified by column chromatography on SiO2 (30% acetone/hexane)

Sources & evidence

ORD record
ord-1c3856b9ce774476878e632fcf9a59ed
Source dataset
uspto-grants-2014_09
Patent number
US08822507B2

Reaction notes

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