Triethylamine → (R)-N,N-Dimethyl-1-(4-nitro-2-(trifluoromethyl)benzyl)pyrrolidin-3-amine

HRID 572987ノート

反応式

HRID 572987 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].CCN(CC)CC.[CH3:23][N:24]([CH3:30])[C@@H:25]1[CH2:29][CH2:28][NH:27][CH2:26]1>C(Cl)Cl>[CH3:23][N:24]([CH3:30])[C@@H:25]1[CH2:29][CH2:28][N:27]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[C:12]([F:15])([F:14])[F:13])[CH2:26]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 468387611-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene

生成物 1

HCID 66735770(R)-N,N-Dimethyl-1-(4-nitro-2-(trifluoromethyl)benzyl)pyrrolidin-3-amine収率 60.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of crude 1-(bromomethyl)-4-nitro-2-(trifluoromethyl)benzene (17.5 mmol, 75% pure) in 40 mL of DCM was added Et3N (2.69 mL, 19.3 mmol) and (R)-(+)-3-(dimethylamino)pyrrolidine (2.0 g, 17.5 mmol). After stirring overnight at ambient temperature under an atmosphere of N2, the reaction solution was concentrated, added aq. NaHCO3 (100 mL), and the resulting mixture extracted with DCM (4×50 mL). The combined organic layer was dried over Na2SO4, filtered, concentrated, and the resulting residue was purified by silica gel chromatography (eluted with 0-10% MeOH/DCM) to provide 3.35 g of product as a yellow oil.

後処理

  1. concentrationthe reaction solution was concentrated
  2. additionadded aq. NaHCO3 (100 mL)
  3. extractionthe resulting mixture extracted with DCM (4×50 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe resulting residue was purified by silica gel chromatography (eluted with 0-10% MeOH/DCM)

出典と根拠

ORDレコード
ord-032070bbef4b4cdf836b5724bfc3d2e9
出典データセット
uspto-grants-2015_05
特許番号
US09029533B2

反応ノート

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