2-(Bromomethyl)-1,3-dichloro-5-methoxybenzene → 1-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one

HRID 2235302ノート

反応式

HRID 2235302 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].Br[CH2:22][C:23]1[C:28]([Cl:29])=[CH:27][C:26]([O:30][CH3:31])=[CH:25][C:24]=1[Cl:32]>>[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH:7]1[CH2:8][CH2:9][CH:10]([N:13]2[CH2:17][CH2:16][CH:15]([CH2:22][C:23]3[C:24]([Cl:32])=[CH:25][C:26]([O:30][CH3:31])=[CH:27][C:28]=3[Cl:29])[C:14]2=[O:18])[CH2:11][CH2:12]1)([CH3:4])([CH3:3])[CH3:2]

参加物

3

反応物 2

HCID 592994792-(Bromomethyl)-1,3-dichloro-5-methoxybenzeneHCID 178455336HCID 178455336、化合物

生成物 1

HCID 684705141-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one収率 49%

実験手順

Using the procedure to synthesize Example 202 and using the reagents of cis-1-[4-(tert-butyl-dimethyl-silanoxy)-cyclohexyl]-pyrrolidin-2-one (Preparation 17) and 2-Bromomethyl-1,3-dichloro-5-methoxy-benzene (Preparation 62). Warm reaction to room temperature, quench with NH4Cl (sat), dilute with diethyl ether, wash with brine, dry over sodium sulfate, filter and evaporate to an oil. Chromatography (silica, 100% hexanes to 75:25 hexanes/EtoAc) yields 1-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one in 49% yield. The silylether is dissolved in THF, treated with 10.0 equivalents of HCl (conc) and allowed to stir at room temperature for 3 h, quench reaction with water, dilute with EtOAc, adjust pH to 7.0, separate, dry over sodium sulfate, filter and evaporate provides the titled compound in 84% yield: Mass spectrum (API-ES positive) m/z=372 (M+H).

後処理

  1. customto synthesize Example 202
  2. temperatureWarm
  3. customreaction to room temperature
  4. customquench with NH4Cl (sat)
  5. additiondilute with diethyl ether
  6. washwash with brine
  7. dry with materialdry over sodium sulfate
  8. filtrationfilter
  9. customevaporate to an oil

出典と根拠

ORDレコード
ord-7725e73ccc5c48c4a97c12fa2697e6b3
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…