Water → Methyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine

HRID 1095494ノート

反応式

HRID 1095494 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([C:10]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][CH2:11]1)=[C:8]=O.[OH-].[Na+].O>C1COCC1>[CH3:8][NH:7][C:10]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:11][CH2:12][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:18][CH2:19]1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 125955658-Isocyanato-8-phenyl-1,4-dioxaspiro[4.5]decaneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 12595582Methyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

LiAlH4 (535 mg, 14.08 mmol) was suspended in dry THF (4 ml) with exclusion of moisture from the atmosphere. 8-Isocyanato-8-phenyl-1,4-dioxaspiro[4.5]decane (2.29 g, 8.8 mmol, dissolved in 40 ml of dry THF) was added dropwise in the course of 20 min. When the addition was complete, the reaction mixture was heated to the boiling point under reflux for 4 h. After cooling, first aqueous THF (1 ml of H2O in 3 ml) was cautiously added to the reaction mixture, while cooling with ice, then 1.7 ml of 15 per cent strength sodium hydroxide solution and finally 5 ml of H2O. The mixture was stirred for 20 min and then filtered over silica gel. The solvent mixture obtained after washing the filter cake with ethyl acetate several times was concentrated to dryness on a rotary evaporator. The desired product was obtained in a yield of 2.1 g (97%) as a viscous oil.

後処理

  1. additionWhen the addition
  2. temperaturethe reaction mixture was heated to the boiling point
  3. temperatureunder reflux for 4 h
  4. temperatureAfter cooling
  5. temperaturewhile cooling with ice
  6. filtrationfiltered over silica gel
  7. customThe solvent mixture obtained
  8. washafter washing the filter cake with ethyl acetate several times
  9. concentrationwas concentrated to dryness on a rotary evaporator

出典と根拠

ORDレコード
ord-74dd9a04b79446bd872a63c28d90691d
出典データセット
uspto-grants-2012_03
特許番号
US08138187B2

反応ノート

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