4-Toluenesulfonyl chloride → 2-Nitro-4-pyrrolidin-1-ylmethyl-benzoic acid methyl ester

HRID 1921086Notes

Reaction equation

HRID 1921086 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13].[CH2:16]([N:18](CC)[CH2:19][CH3:20])[CH3:17].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.N1CCCC1>ClCCl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:18]2[CH2:19][CH2:20][CH2:17][CH2:16]2)=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 31268PyrrolidineHCID 22672700Methyl 4-(hydroxymethyl)-2-nitrobenzoate

Product 1

HCID 574473262-Nitro-4-pyrrolidin-1-ylmethyl-benzoic acid methyl esterYield 44.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxymethyl-2-nitro-benzoic acid methyl ester (2.0 g, 9.47 mmol) in dry dichloromethane (80 mL) under argon, at room temperature, triethylamine (1.6 mL, 10.9 mmol, 1.15 eq.) and then p-toluenesulfonyl chloride (2.08 g, 10.9 mmol, 1.15 eq.) were added. The reaction mixture was stirred at room temperature for 1 h, then pyrrolidine (1.6 mL, 18.94 mmol, 2 eq.) was added and the mixture stirred for additional 24 hours. The solvent was evaporated and the residue purified by flash chromatography on silica gel, using dichloromethane-ethanol 95:5 as eluant, affording the title compound (1.12 g).

Workup

  1. stirringthe mixture stirred for additional 24 hours
  2. customThe solvent was evaporated
  3. customthe residue purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9a25f8d7a84b43b49d86bb7546bb1447
Source dataset
uspto-grants-2012_05
Patent number
US08173659B2

Reaction notes

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