Ammonium Chloride → Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

HRID 2300176

反応式

HRID 2300176 の反応式
Cl[C:2]1(Cl)[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][C:3]1=[O:18].[Cl-].[NH4+]>CO.[Zn]>[O:18]=[C:3]1[CH2:2][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4]1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 9857764Tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

生成物 1

HCID 11195798Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate収率 80.2%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

106.1 g zinc dust was added to a mixture of 62.5 g tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate and 500 ml saturated ammonium chloride in methanol. The mixture was stirred for 1 hr and 20 min at room temperature and filtered through Celite. The filtrate was evaporated, 1 N hydrochloric acid/ethyl acetate was added thereto, and the organic layer was recovered. The extract was washed with water, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated, and the resulting residue was subjected to silica gel column chromatography to give 38.9 g of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate.

後処理

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated
  3. addition1 N hydrochloric acid/ethyl acetate was added
  4. customthe organic layer was recovered
  5. washThe extract was washed with water, saturated sodium bicarbonate and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-38d760197e4b4f2c8c387a4995dfd709
出典データセット
uspto-grants-2002_12
特許番号
US06498159B1

関連ノート

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