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

HRID 467520

反応式

HRID 467520 の反応式
[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

参加物

6

反応物 3

HCID 24758Sodium hydride2 回HCID 73833Benzene, ((2-bromoethoxy)methyl)-2 回HCID 560953Benzyl 3-hydroxypyrrolidine-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31c6ebefc897422a9c8ff8c9e97cc707
出典データセット
uspto-grants-2014_01
特許番号
US08623862B2

関連ノート

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