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p-Toluenesulfonic acid → 1-[2-(4,5-Diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-hydroxynaphthalene

HRID 1741406
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HRID 1741406 반응식
[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][CH2:23][C:24]2=[O:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]1([C:36]2[N:37]=[C:38]([CH2:47][CH2:48][NH2:49])[O:39][C:40]=2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:30]1([C:36]2[N:37]=[C:38]([CH2:47][CH2:48][NH:49][CH:24]3[C:25]4[C:20](=[C:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]5[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH:28]=[CH:27][CH:26]=4)[CH2:21][CH2:22][CH2:23]3)[O:39][C:40]=2[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1.[C:30]1([C:36]2[N:37]=[C:38]([CH2:47][CH2:48][NH:49][CH:19]3[C:20]4[C:25](=[C:24]([OH:29])[CH:23]=[CH:22][CH:21]=4)[CH2:26][CH2:27][CH2:28]3)[O:39][C:40]=2[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 183672692-(4,5-Diphenyl-1,3-oxazol-2-yl)ethan-1-amineHCID 224673025-Tert-butyldiphenylsilyloxy-1-tetralone

생성물 2

HCID 183672931-[2-(4,5-Diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-hydroxynaphthaleneHCID 183674001-[2-(4,5-Diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-(t-butyldiphenylsilyloxy)naphthalene

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 5-(t-butyldiphenylsilyloxy)-1-oxo-1,2,3,4-tetrahydronaphthalene (0.52 g), 2-(4,5-diphenyloxazol-2-yl)ethylamine (0.33 g) and p-toluenesulfonic acid (catalytic amount) in toluene (30 ml) was refluxed for 15 hours with Dean-stark equipment. The solution was evaporated in vacuo and MeOH (10 ml) was added to the residue. To the MeOH solution, NaBH4 (0.21 g) was added at 0° C. After being stirred for 30 minutes at room temperature, the solution was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine. The dried solvent was evaporated in vacuo, and the residue was purified by chromatography on silica gel to give 1-[2-(4,5-diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-(t-butyldiphenylsilyloxy)naphthalene (0.25 g) and 1-[2-(4,5-diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-hydroxynaphthalene (0.11 g). To a solution of 1-[2-(4,5-diphenyloxazol-2-yl)ethylamino]-1,2,3,4-tetrahydro-5-(t-butyldiphenylsilyloxy)naphthalene (0.25 g) in THF (2 ml) was added 1M-THF solution (2 ml) of tetra-n-butyl ammonium fluoride (TBAF). After being stirred for 1 hour at room temperature, the reaction mixture was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[2-(4,5-diphenyloxazol-2-yl) ethylamino]-1,2,3,4-tetrahydro-5-hydroxynaphthalene (0.06 g). MS (m/z): 411 (M+ +1) NMR (CDCl3, δ): 1.65-2.10 (4H, m), 2.38-2.85 (2H, m), 3.12 (2H, t, J=5.9 Hz), 3.22 (2H, t, J=5.9 Hz), 6.60-6.79 (1H, m), 6.89-7.12 (2H, m), 7.20-7.42 (6H, m), 7.52-7.75 (4H, m)

후처리

  1. customThe solution was evaporated in vacuo and MeOH (10 ml)
  2. additionwas added to the residue
  3. additionTo the MeOH solution, NaBH4 (0.21 g) was added at 0° C
  4. customthe solution was evaporated in vacuo
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. customThe dried solvent was evaporated in vacuo
  8. customthe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-3e1c92f3ec6e4516948ded2eff8a1d5b
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05972965

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