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

HRID 380162
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HRID 380162 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8778b90e23074d45aa554b064eb91fc1
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06300344B1

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