Imidazole → (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(t-butyldimethylsilyloxy)pyrrolidine

HRID 975646노트

반응식

HRID 975646 반응식
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CC(C)([O-])C.[K+].[CH2:12]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:20][C@H:19]1[CH2:31][CH2:32]OS(C)(=O)=O)=[O:17])[CH:13]=[CH2:14].O>CN(C)C=O.C(OCC)(=O)C>[CH2:12]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[CH2:20][C@H:19]1[CH2:31][CH2:32][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:17])[CH:13]=[CH2:14]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 15537961(2R,4R)-1-allyloxycarbonyl-2-(2-methanesulfonyloxyethyl)-4-(t-butyldimethylsilyloxy)pyrrolidineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 54510818(2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(t-butyldimethylsilyloxy)pyrrolidine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of imidazole (1.52 in N,N-dimethylformamide (70 ml) were added potassium t-butoxide (2.51 g) and a solution of (2R,4R)-1-allyloxycarbonyl-2-(2-methanesulfonyloxyethyl)-4-(t-butyldimethylsilyloxy)pyrrolidine (8.3 g) in N,N-dimethylformamide (13 ml) at ambient temperature with stirring, and the mixture was stirred at about 60° C. for 1 hour. The reaction mixture was cooled with ice-cooling, and water and ethyl acetate were added thereto. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a mixture of chloroform and methanol (10:0.3, V/V) to give (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(t-butyldimethylsilyloxy)pyrrolidine (11.11 g).

후처리

  1. temperatureThe reaction mixture was cooled with ice-
  2. temperaturecooling
  3. customAfter separation
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe resulting residue was purified by silica gel chromatography
  8. washeluting with a mixture of chloroform and methanol (10:0.3, V/V)

출처 및 근거

ORD 기록
ord-521a718c276946819a1ac5b48f0d1c36
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05608056

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