Lithium Hydroxide → Tert-butyl 1-oxo-8-azaspiro(4.5)decane-8-carboxylate

HRID 8749

反応式

HRID 8749 の反応式
COC([CH:5]1[CH2:9][CH2:8][C:7]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:6]1=[O:22])=O.[OH-].[Li+]>C(O)C.O1CCCC1.O>[O:22]=[C:6]1[C:7]2([CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)[CH2:8][CH2:9][CH2:5]1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 219838978-tert-Butyl 2-methyl 1-oxo-8-azaspiro[4.5]decane-2,8-dicarboxylate

生成物 1

HCID 10848487Tert-butyl 1-oxo-8-azaspiro(4.5)decane-8-carboxylate収率 67.5%

試薬・触媒・溶媒 1

HCID 18504229Ethanol tetrahydrofuran water溶媒

反応条件

温度
90 °C

実験手順

To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate (17.2 g, 0.055 mol) from Step F in a 2:2:1 mixture of ethanol/tetrahydrofuran/water (555 mL) was added pulverized lithium hydroxide (26 g, 1.10 mol). The reaction mixture was heated to 90° C. for 60 h. The reaction mixture was allowed to cool and was then concentrated, dissolved in water and dichloromethane, and extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 11.4 g. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (9.41 g).

後処理

  1. additionwas added
  2. temperatureto cool
  3. concentrationwas then concentrated
  4. dissolutiondissolved in water
  5. extractiondichloromethane, and extracted three times with dichloromethane
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford 11.4 g
  11. customThe residue was purified by flash chromatography
  12. washeluting with 20–30% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-279bb325608143949a9c5045f8750794
出典データセット
uspto-grants-2006_08
特許番号
US07091211B2

関連ノート

読み込み中…