Phenyl isocyanate → [5-((Morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methyl 2-tetrahydropyranyl ether

HRID 10172

Reaktionsgleichung

Reaktionsgleichung von HRID 10172
[CH2:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[N+:10]([CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)([O-])=[O:11].C1(N=C=O)C=CC=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[O:15][CH2:14][C:13]1[CH2:3][CH:2]([CH2:1][N:4]2[CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)[O:11][N:10]=1

Komponenten

6

Edukt 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 136522AllylmorpholineHCID 37486562-(2-Nitroethoxy)tetrahydropyran

Produkt 1

HCID 21978771[5-((Morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methyl 2-tetrahydropyranyl etherAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of N-allylmorpholine (0.76 g, 5.0 mmol) in toluene (10 mL) was added 2-(2-nitroethoxy)tetrahydropyran (1.34 g, 7.7 mmol), phenylisocyanate (2:43 g, 20.1 mmol), and triethylamine (52 mg; 0.5 mmol). The resulting mixture was heated at 55° C. overnight. After cooling to room temperature the formed precipitate was removed by filtration and the remaining solution concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 96/3.75/0.25) to yield 0.63 g (44%) of [5-((morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methyl 2-tetrahydropyranyl ether. MH+ 285, Rf 0.34 (CH2Cl2/MeOH/NH4OH 96/3.75/0.25).

Aufarbeitung

  1. temperatureAfter cooling to room temperature the formed precipitate
  2. customwas removed by filtration
  3. concentrationthe remaining solution concentrated in vacuo
  4. customThe residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 96/3.75/0.25)

Quellen und Nachweise

ORD-Eintrag
ord-f898d1d16b634156866bfd923aef5933
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094779B2

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