Cesium carbonate → tert-butyl [(1S)-2-({1-[6-(cyclobutyloxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate

HRID 2368122노트

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HRID 2368122 반응식
[OH:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][CH:12]([O:15][CH2:16][C@@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18])[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:36]1[CH2:39][CH2:38][CH2:37]1>CN(C=O)C.C(OCC)(=O)C>[CH:36]1([O:1][C:2]2[CH:28]=[CH:27][C:5]3[N:6]=[C:7]([N:9]4[CH2:10][CH2:11][CH:12]([O:15][CH2:16][C@@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH3:18])[CH2:13][CH2:14]4)[O:8][C:4]=3[CH:3]=2)[CH2:39][CH2:38][CH2:37]1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 86658692tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate

생성물 1

HCID 86658708tert-butyl [(1S)-2-({1-[6-(cyclobutyloxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate수율 66.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate (500 mg) in DMF (5 mL) were added cesium carbonate (1.7 g) and bromocyclobutane (265 mg), and the mixture was stirred at room temperature for 15 hr and at 60° C. for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (378 mg).

후처리

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-079273af4e66403fa71fc84c8402e174
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703758B2

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