Trifluoroacetic acid → (S)-methyl 1-amino-2,3-dihydro-1H-indene-5-carboxylate

HRID 64439

반응식

HRID 64439 반응식
COC1C=CC([C@@H]([NH:11][C@@H:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)C)=CC=1.FC(F)(F)C(O)=O.CC1C(C)=C(C)C(C)=C(C)C=1>>[NH2:11][C@@H:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

참가 물질

4

반응물 3

HCID 6422Trifluoroacetic acidHCID 12784PentamethylbenzeneHCID 86713454methyl (1S)-1-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}indane-5-carboxylate

생성물 1

HCID 59460662(S)-methyl 1-amino-2,3-dihydro-1H-indene-5-carboxylate수율 62.1%

반응 조건

온도
70 °C

실험 절차

To 452 mg of methyl (1S)-1-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}indane-5-carboxylate were added 34 ml of trifluoroacetic acid and 1.03 g of pentamethylbenzene, followed by stirring at 70° C. for 4 days, and the solvent was evaporated under reduced pressure. To the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and chloroform to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 165 mg of methyl (1S)-1-aminoindane-5-carboxylate.

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. additionTo the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and chloroform
  3. customa layer separation operation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-7346f4a4800a40d8af71c4b993c44102
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447090B2

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