Sodium Hydroxide → HCID 58495673, compound

HRID 1191013Notes

Reaction equation

HRID 1191013 reaction equation
B.CSC.[C:5]([O:9][C:10]([N:12]([CH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:11])([CH3:8])([CH3:7])[CH3:6].OS([O-])(=O)=O.[K+].[OH-].[Na+]>C1COCC1.CO>[C:5]([O:9][C:10]([N:12]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][NH2:23])=[CH:24][CH:25]=1)[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:11])([CH3:7])([CH3:8])[CH3:6]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 58495443HCID 58495443, compound

Product 1

HCID 58495673HCID 58495673, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, add borane-dimethylsulfide complex (13 mL, 26 mmol, 2M solution in THF) to 4-[N-(tert-butoxycarbonyl)-N-(iso-butyl)-aminomethyl]-benzonitrile (1.5 g, 5.2 mmol) in THF (20 mL) at 0° C. Heat the mixture under reflux overnight. Cool the mixture in an ice-bath and add methanol (20 mL). Warm to room temperature and add KHSO4 (7 g in 50 mL of water). Stir for 2 h at room temperature and basify with 3N aqueous NaOH. Extract with DCM, dry the organic phase over Na2SO4, and concentrate in vacuo. Purify by chromatography on silica gel (150 g) eluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound as an oil (0.72 g, 47%). MS (APCI+) m/z: 293 (M+H)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux overnight
  3. temperatureCool the mixture in an ice-bath
  4. extractionExtract with DCM
  5. dry with materialdry the organic phase over Na2SO4
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel (150 g)
  8. washeluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-5c892fdbd0f141468c4efc391a9fe529
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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