Reaktion #340328

Reaktionsgleichung

pent-1-yne

water

benzyl 4-(2-azidoacetyl)morpholine-2-carboxylate

sodium ascorbate

→

title compound

Benzyl 4-(2-(4-propyl-1H-1,2,3-triazol-1-yl)acetyl)morpholine-2-carboxylate

Lösungsmittel

EtOAc

t-BuOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vessel was sealed
2. 2
   Sonstigeplaced in a 65 deg
3. 3
   Extraktionthe organic layer was extracted with dilute sodium bicarbonate (5 mL), dilute brine (5 mL), and saturated brine (5 mL)
4. 4
   Trocknenwas dried over sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified through silica gel (25 mL)
7. 7
   Wascheneluting with EtOAc

Vorschrift

In a sealable vessel, benzyl 4-(2-azidoacetyl)morpholine-2-carboxylate (0.096 g, 0.32 mmol) was suspended in t-BuOH (1 mL) and water (1 mL) was added. An aqueous solution of sodium ascorbate (1.0 M, 0.032 ml, 0.032 mmol) and an aqueous solution of copper(II) sulfate pentahydrate (0.30 M, 0.079 ml, 0.024 mmol) were added, followed by pent-1-yne (0.040 ml, 0.41 mmol). The vessel was sealed and placed in a 65 deg oil bath, whereupon the mixture was stirred for 14 h. The reaction mixture was cooled to RT, taken up in EtOAc (60 mL), and the organic layer was extracted with dilute sodium bicarbonate (5 mL), dilute brine (5 mL), and saturated brine (5 mL), then was dried over sodium sulfate and concentrated. The residue was purified through silica gel (25 mL) eluting with EtOAc, affording the title compound (105 mg, 0.28 mmol). MS m/z 373 (M+1).

Quelle