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

HRID 1497348노트

반응식

HRID 1497348 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7d4d9e39799c4cd88e58d75b4b364982
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199971B2

반응 노트

불러오는 중…