Tetrahydrofuran → (1r)-1-(4,5-Diphenyloxazol-2-yl)methylamino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 1741363Notes

Reaction equation

HRID 1741363 reaction equation
[N:1]([C@H:4]1[C:13]2[C:8](=[C:9]([O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH2:5]1)=[N+]=[N-].[CH2:32]1[CH2:36][O:35][CH2:34][CH2:33]1>C(O)C.[Pd]>[C:13]1([C:4]2[N:1]=[C:36]([CH2:32][NH:1][C@H:4]3[C:13]4[C:8](=[C:9]([O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[CH:10]=[CH:11][CH:12]=4)[CH2:7][CH2:6][CH2:5]3)[O:35][C:34]=2[C:33]2[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 18393825(1R)-1-azido-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54420662(1r)-1-(4,5-Diphenyloxazol-2-yl)methylamino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1R)-1-azido-5-t-butyldiphenylsilyloxy-1,2,3,4-tetra-hydronaphthalene (0.95 mg) and 10% Pd/C (0.2 g) in a mixture of ethanol (20 ml) and THF (20 ml) was stirred under H2 for 2 hours. The catalyst was filtered off and filtrate was evaporated. The residue was dissolved in DMF (10 ml) and then K2CO3 (600 mg) and (4,5-diphenyloxazol-2-yl)methyl bromide (700 mg) were added thereto. After being stirred for 2 hours at room temperature, the mixture was poured into a 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-(4,5-diphenyloxazol-2-yl)methylamino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.4 g). MS (m/z): 636 (M+ +1) IR (Neat): 3400 cm-1NMR (CDCl3, δ): 1.09 (9H, s), 1.6-2.2 (4H, m), 2.6-3.2 (2H, m), 3.91 (1H, m), 4.06 (2H, s), 6.30 (1H, d, J=8 Hz), 6.72 (1H, t, J=8 Hz), 6.93 (1H, d, J=8 Hz), 7.2-7.8 (10H, m)

Workup

  1. filtrationThe catalyst was filtered off
  2. customfiltrate was evaporated
  3. dissolutionThe residue was dissolved in DMF (10 ml)
  4. additionK2CO3 (600 mg) and (4,5-diphenyloxazol-2-yl)methyl bromide (700 mg) were added
  5. stirringAfter being stirred for 2 hours at room temperature
  6. additionthe mixture was poured into a mixture of ethyl acetate and water
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo
  10. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a5aeee97f68b4da5b8740a43d92a4884
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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