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Pyridine → 3,5-Dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate

HRID 2235320
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인쇄 미리보기

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HRID 2235320 반응식
[Cl:1][C:2]1[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([Cl:22])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16].N1C=CC=CC=1.[O:29](S(C(F)(F)F)(=O)=O)[S:30]([C:33]([F:36])([F:35])[F:34])(=O)=[O:31]>O>[F:34][C:33]([F:36])([F:35])[S:30]([O:21][C:19]1[CH:18]=[C:17]([Cl:22])[C:3]([CH2:4][CH:5]2[CH2:9][CH2:8][N:7]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[C:6]2=[O:16])=[C:2]([Cl:1])[CH:20]=1)(=[O:31])=[O:29]
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참가 물질

5

반응물 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 592994221-Cyclohexyl-3-(2,6-dichloro-4-hydroxy-benzyl)-pyrrolidin-2-one

생성물 1

HCID 592994213,5-Dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate수율 82%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

Charge a flask with 3-(2,6-dichloro-4-hydroxybenzyl)-1-cyclohexylpyrrolidin-2-one (Example 175) (7.5 g, 22 mmol) dissolve with pyridine (200 mL) and cool to 0° C. under nitrogen. Add Tf2O (10 mL, 26 mmol) slowly and warm to room temperature. Stir at room temperature for 30 minutes. Pour into water (1 L) and extract with ether. Wash ether layer twice with water. Dry over sodium sulfate, filter and concentrate. Purify over silica gel (10% ethyl acetate in hexanes) to yield 8.5 g (82%) of the title compound as a white solid. Mass spectrum (apci) rn/z=474.1 (M+H).

후처리

  1. extractionextract with ether
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify over silica gel (10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-e5ba2df14caa49279e865918971fa835
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07713979B2

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