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

HRID 1904914ノート

反応式

HRID 1904914 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 14476557Methyl 1-benzyl-3-phenylpyrrolidine-3-carboxylate収率 41.1%

試薬・触媒・溶媒 2

HCID 62656Caswell No. 736触媒HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b9d5aaa11717453d8dc721d0fc89bbd0
出典データセット
uspto-grants-1989_06
特許番号
US04840956

反応ノート

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