Triethylamine → Thiomorpholine, N-BOC protected

HRID 2376855

Reaktionsgleichung

Reaktionsgleichung von HRID 2376855
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C(OC([O-])=O)([O:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O)=O>O1CCCC1>[N:1]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 67164ThiomorpholineHCID 86600350tert-Butoxycarbonyl dicarbonate

Produkt 1

HCID 21949316Thiomorpholine, N-BOC protectedAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Thiomorpholine (5.0 ml, 53 mmol) was dissolved in tetrahydrofuran (200 ml); triethylamine (8.1 ml, 58 mmol) was added thereto; and the reaction mixture was stirred at room temperature. tert-Butoxycarbonyl dicarbonate (13.3 ml, 58 mmol) was added thereto and the reaction mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure; and the residue was purified by silica gel column (eluent; hexane:ethyl acetate=from 80:20, 75:25 to 70:30) to yield the title compound as colorless crystals (10.4 g, 51 mmol).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 10 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customand the residue was purified by silica gel column (eluent; hexane:ethyl acetate=from 80:20, 75:25 to 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-1291f0e48b6f454687c05243ca8ecd72
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468380B2

Verknüpfte Notizen

Wird geladen…