Lithium diisopropylamide → HCID 178455343、化合物

HRID 2235237ノート

反応式

HRID 2235237 の反応式
[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

参加物

7

反応物 3

HCID 2724682Lithium diisopropylamideHCID 592994282-Bromomethyl-1,3-dichloro-5-benzyloxy-benzeneHCID 178455336HCID 178455336、化合物

生成物 1

HCID 178455343HCID 178455343、化合物

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5492454547e04ca7ae1c57dce96cf43e
出典データセット
uspto-grants-2010_05
特許番号
US07713979B2

反応ノート

読み込み中…