2-Bromo-6-methoxypyridine → [3-(6-Methoxy-2-pyridinyl)-3-oxopropyl]carbamic acid 1,1-dimethylethyl ester

HRID 2179960ノート

反応式

HRID 2179960 の反応式
C([Li])CCC.Br[C:7]1[N:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][CH:8]=1.[CH3:15][C:16]([O:19][C:20](=[O:30])[NH:21][CH2:22][CH2:23][C:24](NCOC)=[O:25])([CH3:18])[CH3:17]>O1CCCC1>[CH3:18][C:16]([O:19][C:20](=[O:30])[NH:21][CH2:22][CH2:23][C:24]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([O:13][CH3:14])[N:12]=1)=[O:25])([CH3:15])[CH3:17]

参加物

5

反応物 3

HCID 2568102-Bromo-6-methoxypyridineHCID 86584230[2-(Methoxymethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl esterHCID 178418339Butyllithium

生成物 1

HCID 86759696[3-(6-Methoxy-2-pyridinyl)-3-oxopropyl]carbamic acid 1,1-dimethylethyl ester収率 73.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Butyl lithium (2.5M solution in hexanes, 1.4 ml) was added to a solution of 6-bromo-2-methoxypyridine (690 mg, 4.0 mmol) in tetrahydrofuran (4 ml) at −78° C. and stirred for 1 h. A solution of [3-(methoxymethylamino)-3-oxopropyl carbamic acid 1,1-dimethylethyl ester (344 mg, 1.42 mmol) in tetrahydrofuran (3 ml) was added and the mixture was warmed to 0° C. over 3 h. The mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (three times) The combined organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluting with petrol-acetone to give the sub-title compound as a colourless oil (291 mg, 73%).

後処理

  1. customThe mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate (three times) The combined organic extracts
  3. dry with materialwere dried (sodium sulphate)
  4. customevaporated
  5. custompurified by chromatography on silica eluting with petrol-acetone

出典と根拠

ORDレコード
ord-560ee9a45df445ab8891d4fb41f77028
出典データセット
uspto-grants-2005_05
特許番号
US06887871B2

反応ノート

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