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

HRID 629227ノート

反応式

HRID 629227 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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 vaccuo 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.

後処理

  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 vaccuo

出典と根拠

ORDレコード
ord-aa16d073eade4126abc5910f75941610
出典データセット
uspto-grants-2016_04
特許番号
US09315498B2

反応ノート

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