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

HRID 380140Notes

Reaction equation

HRID 380140 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).

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-e2b579c1f6564a1db575e0e113c5af8c
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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