Potassium Carbonate → HCID 18367284, compound

HRID 1741411Notes

Reaction equation

HRID 1741411 reaction equation
NC1CCC2C(=CC=CC=2O[Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)C1.C1(C2N=C(CBr)OC=2C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:55]1([C:61]2[N:62]=[C:63]([CH2:72][NH:73][CH:74]3[CH2:83][CH2:82][C:81]4[C:76](=[CH:77][CH:78]=[CH:79][C:80]=4[O:84][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:75]3)[O:64][C:65]=2[C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.C1COCC1>[C:55]1([C:61]2[N:62]=[C:63]([CH2:72][NH:73][CH:74]3[CH2:83][CH2:82][C:81]4[C:76](=[CH:77][CH:78]=[CH:79][C:80]=4[OH:84])[CH2:75]3)[O:64][C:65]=2[C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 5685992-Bromomethyl-4,5-diphenyl-oxazoleHCID 2724141Tetrabutylammonium FluorideHCID 18367245HCID 18367245, compoundHCID 18367328HCID 18367328, compound

Product 1

HCID 18367284HCID 18367284, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-amino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (0.96 g), (4,5-diphenyloxazol-2-yl)methyl bromide (0.80 g) and potassium carbonate (0.41 g) in DMF (14 ml) was stirred for 3.5 hours at room temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine. The dried solvent was evaporated in vacuo to give crude 2-[(4,5-diphenyloxazol-2-yl)methylamino]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene. To a solution of crude 2-[(4,5-diphenyloxazol-2-yl)methylamino]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene in THF (5 ml) was added 1M THF (3 ml) solution of tetrabutylammonium fluoride. After being stirred for 1 hour at room temperature, the 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 2-[(4,5-diphenyloxazol-2-yl)methylamino]-1,2,3,4-tetrahydro-5-hydroxynaphthalene (0.66 g). MS (m/z): 397 (M+ +1) NMR (CDCl3, δ): 1.54-1.84 (2H, m), 2.08-2.22 (1H, m), 2.48-3.20 (5H, m), 4.13 (2H, s), 6.58 (1H, d, J=7.8 Hz), 6.68 (1H, d, J=7.8 Hz), 6.99 (1H, dd, J=7.8, 7.8 Hz), 7.34-7.40 (6H, m), 7.55-7.66 (4H, m)

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. customThe dried solvent was evaporated in vacuo
  4. customto give crude 2-[(4,5-diphenyloxazol-2-yl)methylamino]-1,2,3,4-tetrahydro-5-t-butyldiphenylsilyloxynaphthalene
  5. customthe mixture was partitioned between ethyl acetate and sat. NaHCO3
  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-b62f3c0491494f0dadfafde2ba83c1f5
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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