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Dichloromethane → (1S,2R)-2-(2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)acetaldehyde

HRID 1805326
ノート
印刷プレビュー

反応式

HRID 1805326 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][CH:20](OC)[O:21]C)[C:11]3=[O:25])[CH2:9]2)=[CH:4][CH:3]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[C@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][CH:20]=[O:21])[C:11]3=[O:25])[CH2:9]2)=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58305319(1S,2R)-2-(4-chlorophenyl)-1'-(2,2-dimethoxyethyl)spiro[cyclopropane-1,3'-indolin]-2'-one

生成物 1

HCID 58305328(1S,2R)-2-(2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)acetaldehyde

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
0 °C

実験手順

A suspension of (1R,2S) and (1S,2R)-2-(4-chlorophenyl)-1′-(2,2-dimethoxyethyl) spiro[cyclopropane-1,3′-indolin]-2′-one (1 g) in water (1 mL) was cooled to 0° C. and treated with a mixture of DCM and TFA (1:1, 6 mL) for 2 hours. The reaction mixture was poured into saturated aq. NaHCO3 solution and extracted with DCM (3×6 mL). The combined organic layers were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure. The crude product was used for next step directly without any further purification. LC/MS m/e calcd. for C18H14ClNO2: 311, observed (M+H)+: 312.3.

後処理

  1. extractionextracted with DCM (3×6 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated under reduced pressure
  5. customThe crude product was used for next step directly without any further purification

出典と根拠

ORDレコード
ord-973ce012ac004f74aebe3b2c1df5a710
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354443B2

反応ノート

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