Triethylamine → 1,1-Dimethylethyl 2-[[methyl(methylsulfonyl)amino]methyl]-1-pyrrolidinecarboxylate

HRID 2403410Notes

Reaction equation

HRID 2403410 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]([S:24]([CH3:23])(=[O:26])=[O:25])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53346604tert-butyl 2-((methylamino)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 666177341,1-Dimethylethyl 2-[[methyl(methylsulfonyl)amino]methyl]-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg) in dichloromethane (10 mL) at room temperature was added triethylamine (0.36 mL) and methanesulphonyl chloride (0.20 mL). The reaction mixture was stirred at room temperature for 4 h and then partitioned between dichloromethane (20 mL) and saturated aqueous sodium bicarbonate solution (30 mL). The combined organics were washed with brine (30 mL), dried (MgSO4), reduced in vacuo and purified by column chromatography to give 2-[(methanesulfonyl-methyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a white solid (0.63 g).

Workup

  1. custompartitioned between dichloromethane (20 mL) and saturated aqueous sodium bicarbonate solution (30 mL)
  2. washThe combined organics were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-16ca3788cbf24e789ff63834d8148243
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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