Iodoethane → (rac)-(3aSR,6aRS)-3-Ethyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester

HRID 1497348ノート

反応式

HRID 1497348 の反応式
[C:1]([O:5][C:6]([N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[NH:10][C:9]1=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:20][CH3:21]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[N:10]([CH2:20][CH3:21])[C:9]1=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 67437675(3aSR, 6aRS)-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 123307876(rac)-(3aSR,6aRS)-3-Ethyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester収率 94.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (3aSR,6aRS)-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester (Example 1, step 1) (1.50 g, 6.63 mmol) in 25 ml of DMF was added a 60% suspension of sodium hydride in mineral oil (207 mg, 8.62 mmol, 1.3 equiv.). The suspension was stirred for 45 minutes at room temperature (gas evolution), then iodoethane (1.34 g, 0.696 ml, 8.62 mmol, 1.3 equiv.) was added and the mixture was stirred at room temperature overnight. After concentration in vaccuo and workup with ethyl acetate/water, 1.60 g of a yellow oil were obtained containing mineral-oil drops which was directly used in the next step without further characterization.

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationAfter concentration in vaccuo and workup with ethyl acetate/water

出典と根拠

ORDレコード
ord-7d4d9e39799c4cd88e58d75b4b364982
出典データセット
uspto-grants-2015_12
特許番号
US09199971B2

反応ノート

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