Sodium hydride → Benzyl 3-(2-benzyloxyethoxy)pyrrolidine-1-carboxylate

HRID 467520

반응식

HRID 467520 반응식
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[H-].[Na+].Br[CH2:20][CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:23]([O:22][CH2:21][CH2:20][O:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydride2회HCID 73833Benzene, ((2-bromoethoxy)methyl)-2회HCID 560953Benzyl 3-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 70927043Benzyl 3-(2-benzyloxyethoxy)pyrrolidine-1-carboxylate수율 22.2%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

A solution of 1.29 g of benzyl 3-hydroxypyrrolidine-1-carboxylate in 80 ml of THF is cooled to 0° C., 0.245 g of 60% NaH in oil is added and then 1.26 g of [(2-bromoethoxy)methyl]benzene and 0.108 g of tetrabutylammonium iodide and it is heated at 80° C. for 3 hours. 0.28 g of NaH and 0.40 g of [(2-bromoethoxy)methyl]benzene are added and it is heated at 80° C. for 2 hours. The reaction mixture is concentrated under vacuum, the residue is extracted with DCM, the organic phase is washed with 0.1M HCl solution, with a saturated solution of NaHCO3, it is dried and the solvent is evaporated under vacuum. The product thus obtained is purified by preparative HPLC and 0.46 g of the expected compound is obtained.

후처리

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. extractionthe residue is extracted with DCM
  3. washthe organic phase is washed with 0.1M HCl solution, with a saturated solution of NaHCO3, it
  4. customis dried
  5. customthe solvent is evaporated under vacuum
  6. customThe product thus obtained
  7. customis purified by preparative HPLC

출처 및 근거

ORD 기록
ord-31c6ebefc897422a9c8ff8c9e97cc707
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623862B2

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