Tin tetrachloride → HCID 131733214, compound

HRID 1528210Notes

Reaction equation

HRID 1528210 reaction equation
[Cl:1][C:2]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([O:13][CH3:14])=[O:12])=[O:5].[Sn](Cl)(Cl)(Cl)Cl>CO>[NH2:19][C:18]1[C:2]([Cl:1])=[C:3]([CH:15]=[CH:16][CH:17]=1)[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([O:13][CH3:14])=[O:12])=[O:5]

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 131733215HCID 131733215, compound

Product 1

HCID 131733214HCID 131733214, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.64 g of methyl (S)-1-(2-chloro-3-nitrobenzoyl)pyrrolidine-2-carboxylate and 10.0 g of tin chloride in 60 ml of methanol was refluxed for 1 hour. The reaction medium was filtered and the filtrate was concentrated by half its volume and extracted with ethyl acetate (3×50 ml). The organic phases were combined, dried over magnesium sulfate and evaporated. 2.20 g of methyl (S)-1-(3-amino-2-chlorobenzoyl)pyrrolidine-2-carboxylate were obtained. Yield=92%.

Workup

  1. filtrationThe reaction medium was filtered
  2. concentrationthe filtrate was concentrated by half its volume
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ee15d474abd3479a94a9f974e160bdd8
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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