Triethylamine → Thiomorpholine, N-BOC protected

HRID 2215531

Reaktionsgleichung

Reaktionsgleichung von HRID 2215531
[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 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Thiomorpholine (5.0 ml, 53 mol) was dissolved in tetrahydrofuran (200 ml); triethylamine (8.1 ml, 58 ml) 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-1f78b47ce5144d6ba73f778e4299dc27
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109219B2

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