Lithium diisopropylamide → HCID 178455343, 화합물

HRID 2235237노트

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HRID 2235237 반응식
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([Cl:46])[C:40]([CH2:44]Br)=[C:41]([Cl:43])[CH:42]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1.C([O-])(O)=O.[Na+].CCOC(C)=O>[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([Cl:46])[C:40]([CH2:44][CH:15]2[CH2:16][CH2:17][N:13]([C@H:10]3[CH2:9][CH2:8][C@@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:20])[CH3:19])[CH2:12][CH2:11]3)[C:14]2=[O:18])=[C:41]([Cl:43])[CH:42]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

참가 물질

7

반응물 3

HCID 2724682Lithium diisopropylamideHCID 592994282-Bromomethyl-1,3-dichloro-5-benzyloxy-benzeneHCID 178455336HCID 178455336, 화합물

생성물 1

HCID 178455343HCID 178455343, 화합물

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

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온도
-78 °C

실험 절차

Dissolve 2 g (6.7 mmol) cis-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (Preparation 69) in 40 mL of dry THF and cool to −78° C. Add 4 mL 2M LDA dropwise and continue stirring at −78° C. for 30 minutes. Allow the mixture to warm to −40° C. for 0.5 hour then re-cool to −78° C. Add a solution of 2.3 g (6.6 mmol) of the 5-benzyloxy-2-bromomethyl-1,3-dichloro-benzene (Preparation 70) in 20 mL dry THF dropwise, remove the cooling bath and stir the reaction at ambient temperature for 72 hours. Dilute the mixture with 100 mL saturated aqueous NaHCO3 and 50 mL EtOAc. Separate the layers, dry the organic layer with MgSO4 and concentrate under vacuum to an oil. Purify by chromatography using 80/20 Hex/EtOAc to recover 2.3 g (59%) of the title compound as an oil.

후처리

  1. temperatureAllow the mixture to warm to −40° C. for 0.5 hour
  2. temperaturethen re-cool to −78° C
  3. customremove the cooling bath
  4. stirringstir
  5. customthe reaction at ambient temperature for 72 hours
  6. customSeparate the layers
  7. dry with materialdry the organic layer with MgSO4
  8. concentrationconcentrate under vacuum to an oil
  9. customPurify by chromatography
  10. customto recover 2.3 g (59%) of the title compound as an oil

출처 및 근거

ORD 기록
ord-5492454547e04ca7ae1c57dce96cf43e
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713979B2

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