Trifluoroacetic acid → (3aRS,6aSR)-1-Methyl-hexahydro-cyclopentaimidazol-2-one

HRID 1894238노트

반응식

HRID 1894238 반응식
C(O[C:6]([N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[N:10](C)[C:9]1=[O:17])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:6][N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[NH:10][C:9]1=[O:17]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67437672(3aSR,6aRS)-3-Methyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 59655249(3aRS,6aSR)-1-Methyl-hexahydro-cyclopentaimidazol-2-one수율 92.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3aSR,6aRS)-3-methyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester (Example 106, step 2) (1.99 g, 8.28 mmol) in 30 ml of dichloromethane was added trifluoroacetic acid (7.55 g, 5.1 ml, 66.3 mmol, 8 equiv.) and the yellow solution was stirred at for 5 h at room temperature. The reaction mixture was quenched by addition of saturated sodium bicarbonate solution and the pH of the aqueous phase was set to 9. After workup with dichloromethane/water, the organic phases were dried, filtered and concentrated in vacuo to yield 1.07 g of an off-white solid, which was taken up in cold ethyl acetate and filtered to yield the title compound (822 mg, 71%) as a crystalline white solid which was directly used in the next step without further characterisation.

후처리

  1. customThe reaction mixture was quenched by addition of saturated sodium bicarbonate solution
  2. dry with materialAfter workup with dichloromethane/water, the organic phases were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f060c4495d64438386ce2300eba6dc33
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513273B2

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