Potassium Carbonate → (2R)-2-(4,5-diphenyloxazol-2-yl)-1-(3-ethoxycarbonylmethoxybenzyl)pyrrolidine

HRID 1741427Notes

Reaction equation

HRID 1741427 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][CH2:21][CH2:20][NH:19]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.Br[CH2:24][C:25]1[CH:26]=[C:27]([O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:28]=[CH:29][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:26]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11459982Ethyl 3-(bromomethyl)phenoxyacetateHCID 15505347(2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidine

Product 1

HCID 53927647(2R)-2-(4,5-diphenyloxazol-2-yl)-1-(3-ethoxycarbonylmethoxybenzyl)pyrrolidineYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R)-2-(4,5-diphenyloxazol-2-yl)pyrrolidine (400 mg) and 3-bromomethyl-1-ethoxycarbonylmethoxybenzene (0.76 g) in N,N-dimethylformamide (10 ml) was added K2CO3 (1 g) 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 (2R)-2-(4,5-diphenyloxazol-2-yl)-1-(3-ethoxycarbonylmethoxybenzyl)pyrrolidine (0.27 g). MS (m/z): 483 (M+ +1) IR (Neat): 1750 cm-1NMR (CDCl3, δ): 1.25 (3H, t, J=7.0 Hz), 1.8-2.5 (5H, m), 3.14 (1H, m), 3.60 (1H, d, J=14 Hz), 3.84 (1H, m), 3.85 (1H, d, J=14 Hz), 4.23 (2H, q, J=7.0 Hz), 4.48 (2H, s), 6.71 (1H, d, J=8 Hz), 6.8-7.0 (2H, m), 7.16 (1H, t, J=8.0 Hz), 7.3-7.8 (16H, m)

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water, sat. NaHCO3, and brine
  3. customThe dried solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-fdeaea72e90a40caa33853b5be18fcdf
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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