Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → 4-[1-Benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine

HRID 42631

반응식

HRID 42631 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[C:7]([C:9]([C:11]([F:14])([F:13])[F:12])=[CH2:10])[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.[CH2:21]([N:28]([CH2:32][Si](C)(C)C)[CH2:29]OC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl.FC(F)(F)C(O)=O>[CH2:21]([N:28]1[CH2:32][CH2:10][C:9]([C:7]2[CH:8]=[C:3]([C:2]([F:1])([F:19])[F:20])[N:4]=[C:5]([C:15]([F:18])([F:16])[F:17])[CH:6]=2)([C:11]([F:14])([F:13])[F:12])[CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 866646212,6-Bis(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine

생성물 1

HCID 866749264-[1-Benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine수율 85%

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid촉매HCID 6344Dichloromethane용매2회

실험 절차

To the solution of 2,6-bis(trifluoromethyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine (1.25 g) and N-benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine (5.0 g) in dichloromethane was added dropwise the solution of trifluoroacetic acid (0.038 g) in dichloromethane while cooling with ice. On completion of the dropwise addition, the mixture was warmed to room temperature and stirred over night. The mixture was washed with saturated sodium bicarbonate water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield 4-[1-benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine (1.52 g). 1H-NMR (CDCl3) δ: 2.23-2.29 (1H, m), 2.65-2.69 (2H, m), 2.96 (1H, d), 3.05-3.15 (2H, m), 3.58 (1H, d), 3.82 (1H, d), 7.26-7.37 (5H, m), 8.00 (2H, s).

후처리

  1. temperaturewhile cooling with ice
  2. additionOn completion of the dropwise addition
  3. washThe mixture was washed with saturated sodium bicarbonate water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter the drying agent was filtered off
  6. distillationthe solvent was distilled away under the reduced pressure
  7. customthe residue was then purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-838af80dacb64276b9baca66c568568e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536201B2

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