Dimethyl Sulfoxide → (1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-acetaldehyde

HRID 901061노트

반응식

HRID 901061 반응식
[CH2:1]([C:3]1([CH2:18][CH2:19][OH:20])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2].C(Cl)Cl.CS(C)=O.N1C=CC=CC=1.S(=O)(=O)=O>O>[CH2:1]([C:3]1([CH2:18][CH:19]=[O:20])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 168533Sulfur trioxide-pyridineHCID 108910512-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-ethanol

생성물 1

HCID 20516149(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-acetaldehyde수율 52%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a stirred solution of compound 1 (136 mg, 0.5 mmol), CH2Cl2 (2 mL), dry DMSO (142 μL, 2.0 mmol, 4.0 eq), and dry TEA (697 μL, 5.0 mmol, 10.0 eq) at room temperature under argon, sulfur trioxide-pyridine complex (Pyr-SO3, 318 mg, 2.0 mmol, 4.0 eq) was added in a portion-wise manner and stirred for two days. The resulting mixture was then diluted with water and extracted three times with Et2O. The combined organic phases were dried with Na2SO4, concentrated, and purified by column chromatography using 20:80:EtOAc:Hexane to give a yellow-white solid (70 mg, 52%). Spectral data were identical to those reported above.

후처리

  1. extractionextracted three times with Et2O
  2. dry with materialThe combined organic phases were dried with Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-c3fb4fe9b23546a59fd17778c8b98e28
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361680B2

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