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Triethylamine → (S)-3-methanesulfonyloxy-1-(3-pyrrolidinophenethyl)pyrrolidine

HRID 2251906
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2251906
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:10]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(=O)([O-])O.[Na+]>ClCCl>[CH3:27][S:28]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[CH:10]=2)[CH2:3]1)(=[O:30])=[O:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69199429(S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine

Produkt 1

HCID 86592731(S)-3-methanesulfonyloxy-1-(3-pyrrolidinophenethyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

(S)-3-Hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine (1.04 g, 4.00 mmol) was dissolved in dichloromethane (10 ml). Triethylamine (0.76 ml, 5.49 mmol) and methanesulfonyl chloride (0.39 ml, 5.03 mmol) were added to the obtained solution at 0° C. and they were stirred overnight. The reaction mixture was distributed into 5% aqueous sodium hydrogencarbonate solution and dichloromethane. The organic layer was dried and the solvent was evaporated under reduced pressure. The residue was subjected to the silica gel column chromatography. After the elution with chloroform and methanol (95:5), suitable fractions were collected and the solvent was evaporated under reduced pressure to obtain (S)-3-methanesulfonyloxy-1-(3-pyrrolidinophenethyl)pyrrolidine in the form of a light yellow oily substance (1.30 g, 96%).

Aufarbeitung

  1. customThe organic layer was dried
  2. customthe solvent was evaporated under reduced pressure
  3. washAfter the elution with chloroform and methanol (95:5), suitable fractions
  4. customwere collected
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c4f2ec73e38447bb8eff78300736474a
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07320973B2

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