Ethyl Acetate → (1r)-1-[(2r)-2-(4,5-Diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-ethoxycarbonylmethoxy-1,2,3,4-tetrahydronaphthalene

HRID 1741374Notes

Reaction equation

HRID 1741374 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3[C@H:23]3[C:32]4[C:27](=[C:28]([O:33][Si](C(C)(C)C)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:69]([O:72][CH2:73][CH3:74])(=[O:71])[CH3:70]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3[C@H:23]3[C:32]4[C:27](=[C:28]([O:33][CH2:70][C:69]([O:72][CH2:73][CH3:74])=[O:71])[CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 54043965(1R)-1-[(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 53669336(1r)-1-[(2r)-2-(4,5-Diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-ethoxycarbonylmethoxy-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R)-1-[(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.22 g) in THF (20 ml) was added tetrabutylammonium fluoride (2.7 ml, 1M solution in THF) at 0° C. After being stirred for 2 hours at the room temperature, the mixture was diluted with ethyl acetate and washed with water and brine. The dried solvent was evaporated in vacuo. The obtained oil was dissolved into DMF (10 ml) and then K2CO3 (2.0 g) and ethyl bromoacetate (0.3 ml) were added at room temperature. The mixture was stirred for 2 hours at the same temperature and then partitioned between ethyl acetate and water. The organic layer was washed with water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (1R)-1-[(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-ethoxycarbonylmethoxy-1,2,3,4-tetrahydronaphthalene (800 mg). MS (m/z): 523 (M+ +1) IR (Neat): 1750 cm-1NMR (CDCl3, δ): 1.24 (3H, t, J=7 Hz), 1.5-2.4 (8H, m), 2.5-3.2 (4H, m), 4.0-4.4 (2H, m), 4.22 (2H, q, J=7 Hz), 4.44 (2H, s), 6.37 (1H, d, J=8 Hz), 6.83 (1H, t, J=8 Hz), 7.06 (1H, d, J=8 Hz), 7.2-7.7 (10H, m)

Workup

  1. washwashed with water and brine
  2. customThe dried solvent was evaporated in vacuo
  3. dissolutionThe obtained oil was dissolved into DMF (10 ml)
  4. additionK2CO3 (2.0 g) and ethyl bromoacetate (0.3 ml) were added at room temperature
  5. stirringThe mixture was stirred for 2 hours at the same temperature
  6. custompartitioned between ethyl acetate and water
  7. washThe organic layer was washed with water, sat. NaHCO3 and brine
  8. customThe dried solvent was evaporated in vacuo
  9. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-113348fac0824f1d874ad5a18f9c93e6
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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