Triethylamine → 3-(Methanesulfonyl-methyl-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2365195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365195
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 666176963-(Methanesulfonyl-methyl-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d5864e4cd26045ab9b83398b3b99b631
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697693B2

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