t-Butyl 3-(4-bromophenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate → t-Butyl 1-(4-bromophenyl)-3-oxohexan-2-ylcarbamate

HRID 387416노트

반응식

HRID 387416 반응식
[CH2:1]([Mg]Br)[CH2:2][CH3:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:15](N(OC)C)=[O:16])=[CH:9][CH:8]=1>C1COCC1>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH:14]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[C:15](=[O:16])[CH2:1][CH2:2][CH3:3])=[CH:11][CH:12]=1

참가 물질

4

반응물 2

HCID 18779134t-Butyl 3-(4-bromophenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamateHCID 178455851HCID 178455851, 화합물

생성물 1

HCID 66863791t-Butyl 1-(4-bromophenyl)-3-oxohexan-2-ylcarbamate수율 56.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of propylmagnesium bromide (29.7 g, 201.6 mmol, 3.0 equiv) in THF (200 mL) was added dropwise with stirring at 0° C. to a solution of the carbamate (26 g, 66.5 mmol, 1.0 equiv) in THF (200 mL). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of aqueous NH4Cl (200 mL). The resulting solution was extracted with EtOAc and the organic layers combined. The resulting mixture was washed with saturated NaHCO3 (200 mL) and saturated aqueous NaCl (200 mL), then dried over anhydrous MgSO4. The residue was applied onto a silica gel column with petroleum ether/EtOAc (5:1) to yield t-butyl 1-(4-bromophenyl)-3-oxohexan-2-ylcarbamate (14 g) as a white solid.

후처리

  1. customThe reaction was then quenched by the addition of aqueous NH4Cl (200 mL)
  2. extractionThe resulting solution was extracted with EtOAc
  3. washThe resulting mixture was washed with saturated NaHCO3 (200 mL) and saturated aqueous NaCl (200 mL)
  4. dry with materialdried over anhydrous MgSO4

출처 및 근거

ORD 기록
ord-cabb7e9312514dc5a0911d625ab20199
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372984B2

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