Borane → HCID 69347805, compound

HRID 1373358Notes

Reaction equation

HRID 1373358 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[CH:12]([CH3:16])[CH2:13][C:14]#[N:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.B>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[CH:12]([CH3:16])[CH2:13][CH2:14][NH2:15])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 69347471HCID 69347471, compound

Product 1

HCID 69347805HCID 69347805, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (3RS, 4RS)-4-(4-chlorobenzenesulfonyl)-4-(2,5-difluorophenyl)-3-methylbutyronitrile (2 g, 5.42 mmol) in THF (30 ml) was added borane (1M solution in THF, 6.5 ml, 6.5 mmol) and the mixture was heated at 50° C. for 20 hours. The mixture was cooled to room temperature and quenched with methanol (50 ml) and HCl (2M, 5 ml), then heated at reflux for one hour. The cooled reaction mixture was concentrated in vacuo and purified by flash chromatography eluting with 2% to 10% methanol in dichloromethane, to give as a mixture of diastereoisomers (3RS, 4RS)-4-(4-chlorobenzenesulfonyl)-4-(2,5-difluorophenyl)-3-methylbutylamine as a white solid (1.7 g, 84%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with methanol (50 ml) and HCl (2M, 5 ml)
  3. temperatureheated
  4. temperatureat reflux for one hour
  5. customThe cooled reaction mixture
  6. concentrationwas concentrated in vacuo
  7. custompurified by flash chromatography
  8. washeluting with 2% to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-cb37bb925a0045699a11f0d18646a245
Source dataset
uspto-grants-2007_01
Patent number
US07161006B2

Reaction notes

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