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Potassium Carbonate → Tert-butyl 3-[2-(4-cyanophenoxy)ethyl]-3-azabicyclo[3.2.1]oct-8-yl-(methyl)carbamate

HRID 411534
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인쇄 미리보기

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HRID 411534 반응식
Br[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.[CH:13]12[CH:20]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:17]([CH2:18][CH2:19]1)[CH2:16][NH:15][CH2:14]2.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([O:4][CH2:3][CH2:2][N:15]2[CH2:14][CH:13]3[CH:20]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH:17]([CH2:18][CH2:19]3)[CH2:16]2)=[CH:6][CH:7]=1)#[N:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium Carbonate2회HCID 24522124-(2-Bromoethoxy)benzonitrileHCID 18541001Tert-butyl 3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate

생성물 1

HCID 18540898Tert-butyl 3-[2-(4-cyanophenoxy)ethyl]-3-azabicyclo[3.2.1]oct-8-yl-(methyl)carbamate수율 76%

시약·촉매·용매 2

HCID 6228Dimethylformamide
용매
HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-(2-bromoethoxy)benzonitrile (see step (i) above; 0.94 g, 4.2 mmol), tert-butyl 3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate (Preparation D; 0.91 g, 3.8 mmol) and K2CO3 (0.79 g, 5.7 mmol) in 15 mL of dry DMF was stirred at 90° C. overnight before additional K2CO3 (1 g) was added. The mixture was diluted with 300 mL of DCM, and the mixture was washed with water. The organic layer was separated, dried with Na2SO4 and then evaporated. The crude product was purified by flash chromatography on silica gel, eluting with DCM:MeOH (10:1) containing 0.1% TEA, to yield 1.1 g (76%) of the sub-tide compound.

후처리

  1. additionwas added
  2. washthe mixture was washed with water
  3. customThe organic layer was separated
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel
  7. washeluting with DCM:MeOH (10:1)
  8. additioncontaining 0.1% TEA

출처 및 근거

ORD 기록
ord-af45229c152d45d1a6f430ab5e88bbd5
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06559162B2

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