Diisobutylaluminum hydride → 4-[(3,3-Dimethylbutyl-carbamoyl)-methyl]-benzonitrile

HRID 1191049Notes

Reaction equation

HRID 1191049 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][NH2:5].CC(C[AlH]CC(C)C)C.[C:17]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26](OC)=[O:27])=[CH:21][CH:20]=1)#[N:18]>C1COCC1.CCOC(C)=O>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][NH:5][C:26]([CH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]#[N:18])=[CH:20][CH:21]=1)=[O:27]

Participants

6

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 197093,3-DimethylbutylamineHCID 1512619Methyl (4-cyanophenyl)acetate

Product 1

HCID 584956644-[(3,3-Dimethylbutyl-carbamoyl)-methyl]-benzonitrileYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3,3-dimethylbutylamine (0.8 mL, 6.4 mmol) in anhydrous THF (2 mL) under nitrogen. Cool the solution at 0° C. and add DIBAL-H (6.2 mL, 6.2 mmol, 1M solution in toluene). Allow the mixture to warm up to room temperature and stir for 2 h. Add this complex to a solution of methyl (4-cyanophenyl)acetate (192 mg, 1.1 mmol) in THF (4 mL) and stir at room temperature overnight. Dilute with EtOAc and quench with 5% KHSO4. Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (7:3) to obtain the desired intermediate (160 mg, 60%). MS (ES+) m/z: 245 (M+H)+.

Workup

  1. temperatureAllow the mixture to warm up to room temperature
  2. stirringstir at room temperature overnight
  3. customquench with 5% KHSO4
  4. dry with materialDry the organic phase over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel eluting with hexane/EtOAc (7:3)

Sources & evidence

ORD record
ord-2942c039317647f2a52a1b0e221f3f89
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…