Sodium Hydroxide → HCID 58495631, compound

HRID 1191011Notes

Reaction equation

HRID 1191011 reaction equation
B.CSC.[C:5]([O:9][C:10]([N:12]([CH2:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1)[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[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]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][NH2:25])=[CH:26][CH:27]=1)[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 58495563HCID 58495563, compound

Product 1

HCID 58495631HCID 58495631, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, add borane-dimethylsulfide complex (29.3 mL, 58.7 mmol, 2M solution in THF) to 4-[N-(tert-butoxycarbonyl)-N-(cyclohexyl)-aminomethyl]-benzonitrile (3.7 g, 11.7 mmol) in THF (100 mL) at 0° C. Warm to room temperature and stir overnight. Heat the mixture under reflux for 30 min. Cool the mixture in an ice-bath, and add methanol (20 mL). Warm to room temperature, and add KHSO4 (20 g in 100 mL of water). Stir the mixture for 2 h and adjust the pH to 10 with 3N aqueous NaOH. Extract the mixture with DCM. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (150 g) eluting with a gradient of DCM to 1:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound as an oil (2.43 g, 65%). MS (ES+) m/z: 319 (M+H)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 30 min
  3. temperatureCool the mixture in an ice-bath
  4. temperatureWarm to room temperature
  5. stirringStir the mixture for 2 h
  6. extractionExtract the mixture with DCM
  7. dry with materialDry the organic phase over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify by chromatography on silica gel (150 g)
  11. washeluting with a gradient of DCM to 1:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-34172d60d28146fd9aa895123fdf29f8
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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