3,3-Dimethylbutanal → HCID 57656231, 화합물

HRID 2041457노트

반응식

HRID 2041457 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 57656231HCID 57656231, 화합물수율 37%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a8d997ff7931421dbd9b05993886e31a
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580780B2

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