Oxalyl chloride → (9H-fluoren-9-yl)methyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate

HRID 1619342Notes

Reaction equation

HRID 1619342 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[C:23]([OH:25])=O)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:29])=O>CN(C=O)C.C(Cl)Cl>[Cl:29][C:23]([CH:19]1[CH2:20][CH2:21][CH2:22][N:18]1[C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17])=[O:25]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 1001061-(9H-Fluoren-9-ylmethyl) hydrogen (S)-pyrrolidine-1,2-dicarboxylate

Product 1

HCID 14482361(9H-fluoren-9-yl)methyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidine-2-carboxylic acid (1.2 mg, 3.6 mmol) and 2 drops DMF in DCM was added oxalyl dichloride (2 g, 15.9 mmol), resulting in bubbling of the solution. After the solution stopped bubbling, the reaction solution was concentrated to give the crude product, which was directly used for the next step.

Workup

  1. customresulting
  2. customin bubbling of the solution
  3. customAfter the solution stopped bubbling
  4. concentrationthe reaction solution was concentrated

Sources & evidence

ORD record
ord-48a3d27db6d84f8f9ded394ec439af24
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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