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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
ノート
印刷プレビュー

反応式

HRID 411534 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium Carbonate2 回HCID 24522124-(2-Bromoethoxy)benzonitrileHCID 18541001Tert-butyl 3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide
溶媒
HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-af45229c152d45d1a6f430ab5e88bbd5
出典データセット
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06559162B2

反応ノート

読み込み中…

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