Diethyl Ether → [4-(2-Methoxy-pyridin-3-yl)-4-oxo-butyl]-carbamic acid tert-butyl ester

HRID 352136

反応式

HRID 352136 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(NC(C)C)(C)C.C[Li].COCN[C:22](=O)[CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].C[CH2:35][O:36]CC>O1CCCC1>[CH3:31][C:28]([O:27][C:26](=[O:32])[NH:25][CH2:24][CH2:23][CH2:22][C:35]([C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:36])([CH3:29])[CH3:30]

参加物

7

反応物 5

HCID 3283Diethyl EtherHCID 7912DiisopropylamineHCID 742012-MethoxypyridineHCID 86584230[2-(Methoxymethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl esterHCID 178418348HCID 178418348、化合物

生成物 1

HCID 102539314[4-(2-Methoxy-pyridin-3-yl)-4-oxo-butyl]-carbamic acid tert-butyl ester

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

2-Methoxypyridine (1.9 ml) and then diisopropylamine (0.1 ml) were added to a solution of methyl lithium (10 ml of a 1.6M solution in ether) in tetrahydrofuran (20 ml) at −78° C. and the solution was stirred at 0° C. for 18hand then re-cooled to −78° C. A solution of 1,1-dimethylethyl [3-(methoxymethylamino)-3-oxopropyl]-carbamate (1.6 g) in tetrahydrofuran (5 ml) was added slowly and the resultant solution was allowed to warm to −30° C. over 3.5 h, quenched with aqueous ammonium chloride and extracted with ether (three times). The combined organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluting with petrol-ether gave the sub-title compound as a colourless oil (0.572 g).

後処理

  1. temperaturethen re-cooled to −78° C
  2. temperatureto warm to −30° C. over 3.5 h
  3. customquenched with aqueous ammonium chloride
  4. extractionextracted with ether (three times)
  5. dry with materialThe combined organic extracts were dried (sodium sulphate)
  6. customevaporated
  7. custompurified by chromatography on silica eluting with petrol-ether

出典と根拠

ORDレコード
ord-3e38315d28f442a38cbf626afe239183
出典データセット
uspto-grants-2004_06
特許番号
US06743939B2

関連ノート

読み込み中…