Triethylamine → 1,1-Dimethylethyl 3-[methyl(methylsulfonyl)amino]-1-pyrrolidinecarboxylate

HRID 888943Notes

Reaction equation

HRID 888943 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([S:23]([CH3:22])(=[O:25])=[O:24])[CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 45089533tert-Butyl 3-(methylamino)pyrrolidine-1-carboxylate

Product 1

HCID 666176961,1-Dimethylethyl 3-[methyl(methylsulfonyl)amino]-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-methylamino-pyrrolidine-1-carboxylic acid tert-butyl ester (0.50 g) in dichloromethane (10 ml) was added triethylamine (0.38 ml) followed by methanesulfonyl chloride (0.21 ml). After stirring for 24 hours the reaction mixture was diluted with dichloromethane, washed with sodium bicarbonate solution, dried (Mg2SO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to yield 3-(methanesulfonyl-methyl-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.52 g). Treatment of this compound with HCl in dichloromethane/methanol yielded N-Methyl-N-pyrrolidin-3-yl-methanesulfonamide hydrochloride salt (0.41 g).

Workup

  1. washwashed with sodium bicarbonate solution
  2. dry with materialdried (Mg2SO4)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6548b9a45733427fbe0bcf273af1d5d0
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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