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

HRID 1741406Notes

Reaction equation

HRID 1741406 reaction equation
[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

Participants

6

Reactant 3

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

Product 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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-3e1c92f3ec6e4516948ded2eff8a1d5b
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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