tert-Butyl 4-oxopiperidine-1-carboxylate → 5-fluoro-1-(piperidin-4-yl)-2,3-dihydro-1H-indole

HRID 45583노트

반응식

HRID 45583 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.C([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)(OC(C)(C)C)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:21]1[CH2:22][CH2:23][NH:18][CH2:19][CH2:20]1)[CH2:6][CH2:5]2

참가 물질

7

반응물 4

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 27744635-FluoroindolineHCID 5049666Sodium triacetoxyborohydrideHCID 86585896Sodium bicarbonate water

생성물 1

HCID 674178425-fluoro-1-(piperidin-4-yl)-2,3-dihydro-1H-indole

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-fluoroindoline (1.0 g, 7.30 mmol) and N-Boc-4-piperidone (1.60 g, 7.50 mmol) in tetrahydrofuran (10.0 mL) was added sodium triacetoxyborohydride (1.80 g, 7.50 mmol). After stirring for 3 hours at room temperature, to the mixture were added saturated sodium bicarbonate water and ethyl acetate, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (chloroform/methanol=98/2 to 90/10) to give a Boc derivative of the title compound. MS (ESI+) 321 (M++1, 100%)

후처리

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified with silica gel column (chloroform/methanol=98/2 to 90/10)

출처 및 근거

ORD 기록
ord-e200522c45314eee9bac792acc4c12d9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541585B2

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