N-(2-(p-bromophenoxy)ethyl)pyrrolidine → 5-(Tert-butyl-dimethyl-silyloxy)-2-(7-(tert-butyl-dimethyl-silyloxy)-4-{1-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-ethyl}-2H-chromen-3-yl)phenol

HRID 2055036ノート

反応式

HRID 2055036 の反応式
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH2:16]([Li])CCC.[C:21]([Si:25]([CH3:55])([CH3:54])[O:26][C:27]1[CH:28]=[CH:29][C:30]2[C:31]3[C:44](=[O:45])[O:43][C:42]4[CH:41]=[C:40]([O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[CH:39]=[CH:38][C:37]=4[C:32]=3[CH2:33][O:34][C:35]=2[CH:36]=1)([CH3:24])([CH3:23])[CH3:22].C[Mg]Br>C1COCC1>[C:50]([Si:47]([CH3:49])([CH3:48])[O:46][C:40]1[CH:39]=[CH:38][C:37]([C:32]2[CH2:33][O:34][C:35]3[C:30]([C:31]=2[C:44]([OH:45])([C:2]2[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]4[CH2:13][CH2:12][CH2:11][CH2:10]4)=[CH:4][CH:3]=2)[CH3:16])=[CH:29][CH:28]=[C:27]([O:26][Si:25]([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:55])[CH3:54])[CH:36]=3)=[C:42]([OH:43])[CH:41]=1)([CH3:51])([CH3:52])[CH3:53]

参加物

6

反応物 4

HCID 70657N-(2-(p-bromophenoxy)ethyl)pyrrolidineHCID 115915722,8-bis((tert-butyldimethylsilyl)oxy)chromeno[4,3-c]chromen-5(11H)-oneHCID 178418339ButyllithiumHCID 178418573HCID 178418573、化合物

生成物 1

HCID 219591555-(Tert-butyl-dimethyl-silyloxy)-2-(7-(tert-butyl-dimethyl-silyloxy)-4-{1-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-ethyl}-2H-chromen-3-yl)phenol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 1-[2-(4-bromophenoxy)-ethyl]-pyrrolidine (331 mg, 1.22 mmol) in THF (7.5 mL) at −78° C., was added n-butyl lithium (2.5 M in hexane, 478 μL, 1.19 mmol). The mixture was stirred at −78° C. for 0.5 hours. To this mixture was then added 2,8-bis-(tert-butyl-dimethyl-silyloxy)-11H-chromeno[4,3-c]chromen-5-one (153 mg, 0.30 mmol) in THF (3 mL), prepared as in Example 22. The reaction mixture was then stirred at −78° C. for 1.5 hours. To this mixture was added methyl magnesium bromide (3 M in diethyl ether, 1 mL, 2.99 mmol) at −78° C. and the reaction mixture stirred at room temperature overnight. The reaction was quenched with aqueous NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. The solvent was evaporated to yield the crude product as a yellow oil. The crude product was carried to the next step without further purification.

後処理

  1. stirringThe reaction mixture was then stirred at −78° C. for 1.5 hours
  2. stirringthe reaction mixture stirred at room temperature overnight
  3. customThe reaction was quenched with aqueous NH4Cl
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-85ce62f17f214de8864a5ce197c03095
出典データセット
uspto-grants-2008_02
特許番号
US07329654B2

反応ノート

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