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

HRID 656064ノート

反応式

HRID 656064 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bb399c8976d84b6bb9047be7039af69e
出典データセット
uspto-grants-2011_12
特許番号
US08071584B2

反応ノート

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