3,3-Dimethylbutanal → HCID 57656146, compound

HRID 911599Notes

Reaction equation

HRID 911599 reaction equation
C([Li])CCC.Br[C:7]1[CH:21]=[CH:20][C:10]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:9]([Cl:22])[CH:8]=1.[CH3:23][C:24]([CH3:29])([CH3:28])[CH2:25][CH:26]=[O:27]>C(OCC)C>[C:16]([O:15][C:13]([NH:12][CH2:11][C:10]1[CH:20]=[CH:21][C:7]([CH:26]([OH:27])[CH2:25][C:24]([CH3:29])([CH3:28])[CH3:23])=[CH:8][C:9]=1[Cl:22])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 763353,3-DimethylbutanalHCID 57656181HCID 57656181, compoundHCID 178418339Butyllithium

Product 1

HCID 57656146HCID 57656146, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add butyllithium (11.7 mL, 18.65 mmol) to a solution of 4-bromo-N-(tert-butoxycarbonyl)-2-chloro-benzylamine (2.601 g, 8.11 mmol) in diethyl ether (86 mL) at −78° C. under nitrogen and stir for 2 h. Add 3,3-dimethylbutyraldehyde (1.868 g, 2.3 mL, 18.65 mmol), stir for 30 min at −78° C. and then warm to room temperature. Add water and extract twice the aqueous phase with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting hexane/EtOAc (85:15) to obtain the desired intermediate as a yellow oil (1.825 mg, 66%).

Workup

  1. extractionAdd water and extract twice the aqueous phase with EtOAc
  2. dry with materialDry the combined organic extracts over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel
  6. washeluting hexane/EtOAc (85:15)

Sources & evidence

ORD record
ord-f39f027cee3f488e9dae0adc1f89eea6
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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