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Ammonium Acetate → Methyl 2-amino-5,5-dimethylcyclohex-1-enecarboxylate

HRID 240995
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HRID 240995 반응식
O[C:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]=1[C:10]([O:12][CH3:13])=[O:11].C([O-])(=O)C.[NH4+:18]>C(O)C>[NH2:18][C:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][C:3]=1[C:10]([O:12][CH3:13])=[O:11]
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참가 물질

4

반응물 2

HCID 517165Ammonium AcetateHCID 54676124Methyl 2-hydroxy-5,5-dimethylcyclohex-1-enecarboxylate

생성물 1

HCID 66820389Methyl 2-amino-5,5-dimethylcyclohex-1-enecarboxylate수율 75%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of methyl 2-hydroxy-5,5-dimethylcyclohex-1-enecarboxylate (10.0 g, 54 mmol) and ammonium acetate (10 g, 130 mmol) in ethanol (50 mL) was heated to reflux for 2 hours. The reaction was concentrated to one third original volume, and then diluted with ethyl acetate (100 mL). The organic solution was washed with water (100 mL) and brine (50 mL) and then dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8) to afford methyl 2-amino-5,5-dimethylcyclohex-1-enecarboxylate (7.42 g, 75% yield) as a yellow solid. MS (EI) for C10H17NO2: 184 (MH+).

후처리

  1. temperatureto reflux for 2 hours
  2. concentrationThe reaction was concentrated to one third original volume
  3. additiondiluted with ethyl acetate (100 mL)
  4. washThe organic solution was washed with water (100 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8)

출처 및 근거

ORD 기록
ord-480ddb7ec6be479e9bf452fc258b24b4
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08648066B2

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