2,6-Lutidine → (1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate

HRID 1423411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423411
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C@@H:7]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:8]1.N1C(C)=CC=CC=1C>ClCCl>[CH3:1][S:2]([O:6][C@@H:7]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:19])[CH2:8]1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 216370811,1-Dimethylethyl N-((1S,3R)-3-hydroxycyclopentyl)carbamate

Produkt 1

HCID 86608906(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methansulfonyl chloride (8.2 g; 72.0 mmol) is slowly added to an ice cold solution of commercially available tert-butyl [(1S,3R)-3-hydroxycyclopentyl]carbamate (12.1 g; 60.0 mmol) and 2,6-lutidine (9.6 g; 90.0 mmol) in dry dichloromethane (300 mL). The stirred reaction mixture is allowed to warm to ambient temperature over night. The reaction mixture is extracted with water, ice cold 1N HCl, half saturated brine, and dried over MgSO4. After filtration through a pad of neural alumina (act. 2-3) the solvent is removed under reduced pressure to yield the crude title compound as yellow oil that is processed without additional purification.

Aufarbeitung

  1. customThe stirred reaction mixture
  2. extractionThe reaction mixture is extracted with water, ice cold 1N HCl, half saturated brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration through a pad of neural alumina (act. 2-3) the solvent
  5. customis removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-11adf07ec9fc4d51b1e14b959f0f4852
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927557B2

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