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

HRID 1696330

Reaktionsgleichung

Reaktionsgleichung von HRID 1696330
[N:1]([CH2:4][C:5]([N:7]1[CH2:12][CH2:11][O:10][CH:9]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:8]1)=[O:6])=[N+:2]=[N-:3].O.O=[C:25]1O[C@H:30]([C@H:32](CO)O)[C:28]([O-])=[C:26]1O.[Na+].C#CCCC>CC(O)(C)C.CCOC(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:28]([C:26]1[N:3]=[N:2][N:1]([CH2:4][C:5]([N:7]2[CH2:12][CH2:11][O:10][CH:9]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:8]2)=[O:6])[CH:25]=1)[CH2:30][CH3:32]

Komponenten

8

Edukt 4

HCID 962WaterHCID 123091-PentyneHCID 23667548Sodium AscorbateHCID 86614022Benzyl 4-(2-azidoacetyl)morpholine-2-carboxylate

Produkt 1

HCID 66845266Benzyl 4-(2-(4-propyl-1H-1,2,3-triazol-1-yl)acetyl)morpholine-2-carboxylateAusbeute 875 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. customThe vessel was sealed
  2. customplaced in a 65 deg
  3. extractionthe organic layer was extracted with dilute sodium bicarbonate (5 mL), dilute brine (5 mL), and saturated brine (5 mL)
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified through silica gel (25 mL)
  7. washeluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-fadfb4c76e6a4a73bf12dd1f27192d6d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163766B2

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