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Methyl 3-bromopropanoate → Methyl 3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionate

HRID 13857
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HRID 13857 반응식
Br[CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15](=[O:29])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:10][CH2:9]1.CCN(C(C)C)C(C)C>C(#N)C>[CH3:7][O:6][C:4](=[O:5])[CH2:3][CH2:2][N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15](=[O:29])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][CH2:13]1
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참가 물질

5

반응물 3

HCID 76934Methyl 3-bromopropanoateHCID 81531DiisopropylethylamineHCID 10851461Biphenyl-2-ylcarbamic Acid Piperidin-4-yl Ester

생성물 1

HCID 57459436Methyl 3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionate수율 70%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

Methyl 3-bromopropionate (553 μL, 5.07 mmol) was added to a stirred solution of biphenyl-2-ylcarbamic acid piperidin-4-yl ester (1.00 g, 3.38 mmol; prepared as described in Preparation 1) and DIPEA (1.76 mL, 10.1 mmol) in ACN (34 mL) at 50° C. and the reaction mixture was heated at 50° C. overnight. The solvent was then removed under reduced pressure, and the residue was dissolved in DCM (30 mL). The resulting solution was washed with saturated aqueous sodium bicarbonate solution (10 mL), dried over MgSO4, filtered and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography (5-10% MeOH/DCM) to give 905 mg of the title intermediate (70% yield).

후처리

  1. customThe solvent was then removed under reduced pressure
  2. dissolutionthe residue was dissolved in DCM (30 mL)
  3. washThe resulting solution was washed with saturated aqueous sodium bicarbonate solution (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe crude residue was purified by column chromatography (5-10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-d5ce28f4093644dea52f9b79850cc92e
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728144B2

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