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

HRID 10172

Reaction equation

HRID 10172 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 21978771[5-((Morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methyl 2-tetrahydropyranyl etherYield 44.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f898d1d16b634156866bfd923aef5933
Source dataset
uspto-grants-2006_08
Patent number
US07094779B2

Linked notes

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