3,3-Dimethylbutanal → HCID 57656231、化合物

HRID 911592ノート

反応式

HRID 911592 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 57656231HCID 57656231、化合物収率 37%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-e5e2f69ec29d4a98a5da7a60262e0ff7
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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