Hydrochloric Acid → 4-{1-(3,4-Dimethoxyphenoxy)-4-[8-(methylamino)-3-azabicyclo-[3.2.1]oct-3-yl]butyl}benzonitrile

HRID 411531ノート

反応式

HRID 411531 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)[CH2:10][CH2:11][CH2:12][N:13]2[CH2:19][CH:18]3[CH:20]([N:21](C)[C:22](=O)[O:23]C(C)(C)C)[CH:15]([CH2:16][CH2:17]3)[CH2:14]2)=[CH:5][CH:4]=1)#[N:2].Cl>C(OCC)(=O)C>[OH-:23].[NH4+:2].[CH3:40][O:39][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][C:34]=1[O:37][CH3:38])[O:30][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[CH2:10][CH2:11][CH2:12][N:13]1[CH2:19][CH:18]2[CH:20]([NH:21][CH3:22])[CH:15]([CH2:16][CH2:17]2)[CH2:14]1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 18540880Tert-butyl 3-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate

生成物 2

HCID 14923Ammonium HydroxideHCID 185409394-{1-(3,4-Dimethoxyphenoxy)-4-[8-(methylamino)-3-azabicyclo-[3.2.1]oct-3-yl]butyl}benzonitrile収率 120.8%

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-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate (see step (iv) above; 2.67 g, 4.86 mmol) in ethyl acetate saturated with HCl (60 mL) was stirred overnight at 25° C. under nitrogen. The mixture was partitioned with water (100 mL) and ethyl acetate (50 mL). The aqueous layer was washed with ethyl acetate (50 mL) before being separated, basified with saturated sodium bicarbonate (50 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 (92:7:1), to afford 1.32 g (61%) of the title compound as a yellow oil.

後処理

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

出典と根拠

ORDレコード
ord-fd5eaa59aa07495792cae7183a5d8028
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…