Carbon Dioxide → 1h-Indole-1,7-dicarboxylic acid,6-fluoro-2,3-dihydro-,1-(1,1-dimethylethyl)ester

HRID 387303노트

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HRID 387303 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.CN(CCN(C)C)C.[Li]C(CC)C.[C:31](=[O:33])=[O:32]>CCOCC.O>[CH3:15][C:14]([O:13][C:11]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[C:10]=2[C:31]([OH:33])=[O:32])[CH2:6][CH2:7]1)=[O:12])([CH3:17])[CH3:16]

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 17985580Tert-butyl 6-fluoroindoline-1-carboxylateHCID 178418400CID 53628100

생성물 1

HCID 593326451h-Indole-1,7-dicarboxylic acid,6-fluoro-2,3-dihydro-,1-(1,1-dimethylethyl)ester수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

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온도
-78 °C

실험 절차

To a stirred solution of 1,1-dimethylethyl 6-fluoro-2,3-dihydro-1H-indole-1-carboxylate (8.7 g, 0.037 mol) in Et2O (150 mL) at −78° C. was added TMEDA (7.2 mL, 0.048 mol) and a solution of 1M sec-BuLi (44 mL, 0.044 mol) dropwise. The reaction mixture was stirred for 1 h at −78° C. and then poured onto crushed CO2 (250 mL). The mixture was allowed to warm to room temperature overnight. The suspension was diluted with water (200 mL) and diethyl ether (50 mL), and the layers were separated. The aqueous fraction was acidified with 1M HCl and extracted with diethyl ether (3×100 mL). The combined organic layers were washed with brine (1×50 mL), dried (Na2SO4), and concentrated under reduced pressure giving 8.0 g (77%) of the title compound.

후처리

  1. additionpoured
  2. temperatureto warm to room temperature overnight
  3. customthe layers were separated
  4. extractionextracted with diethyl ether (3×100 mL)
  5. washThe combined organic layers were washed with brine (1×50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-12ad61ce5ac04d818d4a51b5a1fe53f6
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372875B2

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