Triethylamine → (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine

HRID 383396

反応式

HRID 383396 の反応式
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:12][C@H:13]1[CH2:17][CH2:16][CH2:15][NH:14]1.F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([C:28]([F:31])([F:30])[F:29])[CH:20]=1.C(N(CC)CC)C>C(#N)C>[CH3:12][C@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([C:28]([F:29])([F:31])[F:30])[CH:20]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 44118660(S)-2-Methylpyrrolidine 4-methylbenzenesulfonate

生成物 1

HCID 59395009(S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine収率 100.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
82 °C

実験手順

To a solution of (S)-2-methylpyrrolidine tosylate (10.6 g, 41.2 mmol) in acetonitrile (85 mL) was added 4-fluoro-1-nitro-2-(trifluoromethyl)benzene (6.6 g, 31.7 mmol) dropwise and followed by triethylamine (11.0 mL, 79.3 mmol) dropwise. The reaction was heated at 82° C. for 16 h. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with 1N HCl, then dried over Na2SO4 and concentrated in vacuo to yield (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (8.7 g, quantitative yield). LC/MS m/z 275.3 [M+H]+.

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 1N HCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5026c783114c4fe5bc0d8d53c1c77604
出典データセット
uspto-grants-2013_02
特許番号
US08367660B2

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