2-Methyl-2-butene → 3-(1H-indol-3-yl)butanoic acid

HRID 1837859노트

반응식

HRID 1837859 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]([CH3:14])[CH2:11][CH:12]=[O:13])=[CH:2]1.CC(=CC)C.[O-:20]Cl=O.[Na+]>C(O)(C)(C)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]([CH3:14])[CH2:11][C:12]([OH:20])=[O:13])=[CH:2]1

참가 물질

5

반응물 3

HCID 105532-Methyl-2-buteneHCID 234962763-(1H-Indol-3-yl)-butanalHCID 23668197Sodium Chlorite

생성물 1

HCID 2738003-(1H-indol-3-yl)butanoic acid

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

3-(1H-Indol-3-yl)-butanal (130 mg, 0.690 mmol) was dissolved in tert-butyl alcohol (27 mL) and 2-methyl-2-butene (4.7 mL) and subsequently was stirred for 10 min. To this solution was added an aqueous solution (4.7 mL) of NaClO2 (75 mg, 0.83 mmol) and NaH2PO4 (115 mg, 0.830 mmol) in one portion. The reaction mixture was stirred at room temperature for 12 h. The organics were removed by concentrating in vacuo. The residue was diluted with 10 mL of H2O, and adjusted to a neutral pH with 1M HCl. Extraction with EtOAc (3×10 mL), drying over Na2SO4, and concentration in vacuo provided 3-(1H-indol-3-yl)-butanoic acid. TMS-diazomethane was added dropwise to a solution of the crude 3-(1H-indol-3-yl)-butanoic acid in methanol (7 mL) until a yellow color persisted. The residual TMS-diazomethane was quenched by the dropwise addition of acetic acid until the yellow color disappeared. The reaction was then treated with an excess of saturated aqueous sodium bicarbonate, extracted with Et2O (3×20 ml), dried over Na2SO4 and purified by silica gel chromatography (20:80 EtOAc/hexanes to provide (R)-3-(1H-indol-3-yl)-butyric acid methyl ester. [α]D=−7.6 (c=1.0 benzene); reported rotation for (S)-3-(1H-indol-3-yl)-butyric acid methyl ester [α]D=+10.9 (c=2.12, benzene).

후처리

  1. customThe organics were removed
  2. concentrationby concentrating in vacuo
  3. additionThe residue was diluted with 10 mL of H2O
  4. extractionExtraction with EtOAc (3×10 mL)
  5. dry with materialdrying over Na2SO4, and concentration in vacuo

출처 및 근거

ORD 기록
ord-fc6c7b36378b4187a26e400e19e45a4d
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784323B2

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