Acetonitrile → Methyl 1-benzyl-3-phenylpyrrolidine-3-carboxylate

HRID 1904914

반응식

HRID 1904914 반응식
[CH2:1]([N:8]([CH2:14][C:15]#N)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:27][CH3:28])(=[O:26])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=C.C(#N)C>C(Cl)(Cl)Cl.[Ag]F>[C:20]1([C:18]2([C:17]([O:27][CH3:28])=[O:26])[CH2:15][CH2:14][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 3

HCID 6342AcetonitrileHCID 193334Methyl atropateHCID 560960N-Benzyl-N-(trimethylsilylmethyl)aminoacetonitrile

생성물 1

HCID 14476557Methyl 1-benzyl-3-phenylpyrrolidine-3-carboxylate수율 41.1%

시약·촉매·용매 2

HCID 62656Caswell No. 736촉매HCID 6212Chloroform용매

실험 절차

A suspension of 53.4 g (0.23 mol) of N-benzyl-N-(cyanomethyl)-N-[(trimethylsilyl)methyl]amine (J. Org. Chem., 50, 4006 (1985)), 41.2 g (0.25 mol) of methyl atropate, 32.2 g (0.25 mol) of silver fluoride and 1 l of acetonitrile was stirred overnight at room temperature in the dark. The mixture was diluted with chloroform and filtered through celite. Concentration of the filtrate gave an oil which was chromatographed on silica gel, eluting with an 80:20 chloroform:ethyl acetate mixture, to give 27.9 g of methyl 3-phenyl-1-(phenylmethyl)-3-pyrrolidinecarboxylate.

후처리

  1. filtrationfiltered through celite
  2. customConcentration of the filtrate gave an oil which
  3. customwas chromatographed on silica gel
  4. washeluting with an 80:20 chloroform

출처 및 근거

ORD 기록
ord-b9d5aaa11717453d8dc721d0fc89bbd0
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04840956

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