Acetonitrile → 1-Benzyl-3-methylpyrrolidine-3-carbonitrile

HRID 622379

반응식

HRID 622379 반응식
[CH2:1](N(CC#N)C[Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](#[N:21])[C:18]([CH3:20])=[CH2:19].[C:22](#[N:24])C.[C:25](OCC)(=O)C>C(Cl)(Cl)Cl.[Ag]F>[CH3:19][C:18]1([C:22]#[N:24])[CH2:20][CH2:25][N:21]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17]1

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 31368MethacrylonitrileHCID 560960N-Benzyl-N-(trimethylsilylmethyl)aminoacetonitrile

생성물 1

HCID 50864491-Benzyl-3-methylpyrrolidine-3-carbonitrile

시약·촉매·용매 2

HCID 62656Caswell No. 736촉매HCID 6212Chloroform용매2회

실험 절차

A suspension of 11.6 g (0.05 mole) of N-benzyl-N-(cyanomethyl)-N-[(trimethylsilyl)methyl]amine [J. Org. Chem., 50, 4006 (1985)], 3.5 g (0.052 mole) of methacrylonitrile, 7.0 g (0.55 mole) of silver fluoride, and 150 ml of acetonitrile was stirred overnight at room temperature in the dark. The mixture was then diluted with chloroform (150 ml) and filtered through Celite. Concentration of the filtrate gave an oil which was subjected to silica gel chromatography using an 80:20 chloroform:ethyl acetate mixture as the eluent. The major fraction contained 2.5 g of the titled compound.

후처리

  1. filtrationfiltered through Celite
  2. customConcentration of the filtrate gave an oil which

출처 및 근거

ORD 기록
ord-eefa92c9b3ea45d0abd3712bad8c3c76
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04771055

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