5-Tert-butyldiphenylsilyloxy-1-tetralone → (1R)-1-[[(1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl) butyl]amino]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 380101Notes

Reaction equation

HRID 380101 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@@H:5]([NH2:23])[C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1.[Si:24]([O:41][C:42]1[CH:51]=[CH:50][CH:49]=[C:48]2[C:43]=1[CH2:44][CH2:45][CH2:46][C:47]2=O)([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:1][CH2:2][CH2:3][CH2:4][C@@H:5]([NH:23][C@H:47]1[C:48]2[C:43](=[C:42]([O:41][Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:51]=[CH:50][CH:49]=2)[CH2:44][CH2:45][CH2:46]1)[C:6]1[O:7][C:8]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1

Participants

5

Reactant 2

HCID 224673025-Tert-butyldiphenylsilyloxy-1-tetraloneHCID 54014820(1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine

Product 1

HCID 54421594(1R)-1-[[(1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl) butyl]amino]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthaleneYield 78.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

The mixture of (1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butylamine (5.8 g), 5-tert-butyldiphenylsilyloxy-1-tetralone (11 g) and p-toluenesulphonic acid (32 mg) in toluene (150 ml) was heated under reflux in Dean-Stark apparatus for 48 hours. After the solvent was removed in vacuo, the residue was dissolved in a mixture of methanol (50 ml) and THF (200 ml) and NaBH4(0.4 g) was added to the solution at −78° C. After being stirred for 4 hours at the same temperature, the solution was allowed to stand at the room temperature for 30 minutes, then poured into the mixture of ethyl acetate and water. The organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (1R)-1-[[(1R)-4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butyl]amino]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (10.2 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in Dean-Stark apparatus for 48 hours
  3. customAfter the solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in a mixture of methanol (50 ml) and THF (200 ml) and NaBH4(0.4 g)
  5. additionwas added to the solution at −78° C
  6. waitto stand at the room temperature for 30 minutes
  7. additionpoured into the mixture of ethyl acetate and water
  8. washThe organic layer was washed with water and brine
  9. dry with materialdried over MgSO4
  10. customevaporated in vacuo
  11. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8f9196c333a1437694db50c1d94e831f
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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