Dimethylamine → N,N-Dimethyl-1,4-dioxaspiro[4.5]decan-8-amine

HRID 440939ノート

反応式

HRID 440939 の反応式
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[CH3:12][NH:13][CH3:14].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][CH:7]([N:13]([CH3:14])[CH3:12])[CH2:6][CH2:5]2)[O:3][CH2:2]1

参加物

5

反応物 3

HCID 674DimethylamineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 361167N,N-Dimethyl-1,4-dioxaspiro[4.5]decan-8-amine収率 85%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 5.0 gm (32 mMol) 1,4-cyclohexanedione mono-ethylene ketal and 10.80 gm (240 mMol) dimethylamine were added 2.0 mL acetic acid and the mixture was stirred at 0° C. for 1.5 hours. To this solution were then added 3.62 gm (58 mMol) sodium cyanoborohydride and the reaction stirred for an additional hour at ambient. The pH of the reaction mixture was adjusted to ~7 with 16 mL acetic acid and stirred 18 hours at ambient. The volatiles were removed under reduced pressure and the residue dissolved in cold 5% tartaric acid solution and then the aqueous phase was made basic with 5N sodium hydroxide. This aqueous phase was extracted well with dichloromethane. These organic extracts were combined and concentrated under reduced pressure to give 5.04 gm (85%) of the title compound as an oil.

後処理

  1. stirringthe reaction stirred for an additional hour at ambient
  2. stirringstirred 18 hours at ambient
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue dissolved in cold 5% tartaric acid solution
  5. extractionThis aqueous phase was extracted well with dichloromethane
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-89a7f7004d1e4d63b24ea97d008de492
出典データセット
uspto-grants-1996_05
特許番号
US05521197

反応ノート

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