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

HRID 10172

反応式

HRID 10172 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f898d1d16b634156866bfd923aef5933
出典データセット
uspto-grants-2006_08
特許番号
US07094779B2

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