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

HRID 10172

반응식

HRID 10172 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
55 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f898d1d16b634156866bfd923aef5933
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094779B2

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