3,3-Dimethylbutanal → HCID 57655962, compound

HRID 911589Notes

Reaction equation

HRID 911589 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])=[CH:9][C:8]=1[F:22].[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])=[C:8]([F:22])[CH:9]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 763353,3-DimethylbutanalHCID 57656266HCID 57656266, compoundHCID 178418339Butyllithium

Product 1

HCID 57655962HCID 57655962, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add butyllithium (7.3 mL, 11.7 mmol) to a solution of 4-bromo-N-(tert-butoxycarbonyl)-3-fluoro-benzylamine (1.55 g, 5.1 mmol) in diethyl ether (54 mL) at −78° C. under nitrogen and stir for 30 min. Add 3,3-dimethylbutyraldehyde (562 mg, 0.7 mL, 5.6 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 with hexane/EtOAc (85:15) to obtain the desired intermediate as a yellow oil (394 mg, 24%).

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 eluting with hexane/EtOAc (85:15)

Sources & evidence

ORD record
ord-5881dae9d56b491c9234d6aaa28c2a37
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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