3,3-Dimethylbutanal → HCID 57656231, compound

HRID 2041457Notes

Reaction equation

HRID 2041457 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]([F: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[F:22])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 763353,3-DimethylbutanalHCID 53432589tert-Butyl [(4-bromo-2-fluorophenyl)methyl]carbamateHCID 178418339Butyllithium

Product 1

HCID 57656231HCID 57656231, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add butyllithium (14.2 mL, 22.7 mmol) to a solution of 4-bromo-N-(tert-butoxycarbonyl)-2-fluoro-benzylamine (3 g, 9.9 mmol) in diethyl ether (105 mL) at −78° C. under nitrogen and stir for 30 min. Add 3,3-dimethylbutyraldehyde (1.086 g, 1.4 mL, 10.8 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 (1.179 g, 37%).

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-a8d997ff7931421dbd9b05993886e31a
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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