Potassium Carbonate → Tert-butyl 3-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate

HRID 411530ノート

反応式

HRID 411530 の反応式
[CH:1]12[CH:8]([N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.CS(O[CH2:23][CH2:24][CH2:25][CH:26]([C:38]1[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=1)[O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:44]([C:41]1[CH:40]=[CH:39][C:38]([CH:26]([O:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=2)[CH2:25][CH2:24][CH2:23][N:3]2[CH2:4][CH:5]3[CH:8]([N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:1]([CH2:7][CH2:6]3)[CH2:2]2)=[CH:43][CH:42]=1)#[N:45]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 18541001Tert-butyl 3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamateHCID 218675684-(4-Cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl methanesulfonate

生成物 1

HCID 18540880Tert-butyl 3-[4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl]-3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate収率 60.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of tert-butyl 3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate (Preparation D; 2.60 g, 10.9 mmol), 4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl methanesulfonate (see step (iii) above; 4.40 g, 10.9 mmol), and potassium carbonate (1.50 g, 10.9 mmol) in DMF (50 mL) was heated at 90° C. under nitrogen for 4 h. The mixture was partitioned with water (50 mL) and diethyl ether (50 mL). The aqueous layer was extracted with diethyl ether (2×50 mL). The combined organic extracts were washed with brine (2×30 mL), dried (Na2SO4), filtered and then concentrated in vacuo. The residue was chromatographed on silica gel, eluting with dichloromethane:methanol (98:2), to afford 3.60 g (60%) of the sub-title compound as an amorphous solid.

後処理

  1. customThe mixture was partitioned with water (50 mL) and diethyl ether (50 mL)
  2. extractionThe aqueous layer was extracted with diethyl ether (2×50 mL)
  3. washThe combined organic extracts were washed with brine (2×30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluting with dichloromethane:methanol (98:2)

出典と根拠

ORDレコード
ord-c95062bd67c04494a8d36f07695feaa9
出典データセット
uspto-grants-2003_05
特許番号
US06559162B2

反応ノート

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