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

HRID 411521ノート

反応式

HRID 411521 の反応式
[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

参加物

5

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c50fa3ccae14ad08327660253e16939
出典データセット
uspto-grants-2003_05
特許番号
US06559162B2

反応ノート

読み込み中…