Hydrochloric Acid → 4-[2-Hydroxy-3-[8-(methylamino)-3-azabicyclo[3.2.1]oct-3-yl]-propoxy}benzonitrile

HRID 411521노트

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HRID 411521 반응식
[C:1]([C:3]1[CH:30]=[CH:29][C:6]([O:7][CH2:8][CH:9]([OH:28])[CH2:10][N:11]2[CH2:17][CH:16]3[CH:18]([N:19](C)[C:20](=O)OC(C)(C)C)[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].Cl>C(OCC)(=O)C>[OH-:7].[NH4+:2].[OH:28][CH:9]([CH2:10][N:11]1[CH2:12][CH:13]2[CH:18]([NH:19][CH3:20])[CH:16]([CH2:15][CH2:14]2)[CH2:17]1)[CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:30][CH:29]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 18540975Tert-butyl 3-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3-azabicyclo-[3.2.1]oct-8-yl(methyl)carbamate

생성물 2

HCID 14923Ammonium HydroxideHCID 185408844-[2-Hydroxy-3-[8-(methylamino)-3-azabicyclo[3.2.1]oct-3-yl]-propoxy}benzonitrile수율 192.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

A suspension of tert-butyl 3-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate (see step (i) above; 3.15 g, 7.58 mmol) in ethyl acetate saturated with HCl (40 mL) was stirred for 5 h at 25° C. under nitrogen. The mixture was partitioned with water (100 mL) and ethyl acetate (50 mL). The aqueous layer was separated and washed with ethyl acetate. The aqueous layer was separated, basified with saturated sodium bicarbonate (30 mL) and then extracted with dichloromethane (3×50 mL). The organic extracts were dried (Na2SO4), filtered, concentrated in vacuo and then chromatographed on silica gel, eluting with dichloromethane:methanol:concentrated ammonium hydroxide (88:10:2), to afford 2.30 g (96%) of the title compound as a colorless oil.

후처리

  1. customThe mixture was partitioned with water (100 mL) and ethyl acetate (50 mL)
  2. customThe aqueous layer was separated
  3. washwashed with ethyl acetate
  4. customThe aqueous layer was separated
  5. extractionextracted with dichloromethane (3×50 mL)
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel
  10. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-1c50fa3ccae14ad08327660253e16939
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559162B2

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