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

HRID 1904914Notes

Reaction equation

HRID 1904914 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 62656Caswell No. 736CatalystHCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b9d5aaa11717453d8dc721d0fc89bbd0
Source dataset
uspto-grants-1989_06
Patent number
US04840956

Reaction notes

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