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 2055036노트

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HRID 2055036 반응식
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]

참가 물질

6

반응물 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, 화합물

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-85ce62f17f214de8864a5ce197c03095
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329654B2

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