Tetrahydrofuran → (1-Benzhydrylazetidin-3-yl)methanol

HRID 1091288ノート

反応式

HRID 1091288 の反応式
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:13][C:14]([CH:16]1[CH2:19][N:18]([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17]1)=O.[OH-].[Na+]>O>[CH:20]([N:18]1[CH2:19][CH:16]([CH2:14][OH:13])[CH2:17]1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 14798Sodium HydroxideHCID 2759842Methyl 1-(diphenylmethyl)azetidine-3-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 2758715(1-Benzhydrylazetidin-3-yl)methanol収率 108.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To an anhydrous tetrahydrofuran solution (100 mL) of lithium aluminum hydride (1.14 g, 29.93 mmol), a tetrahydrofuran solution (50 mL) of 1-benzhydrylazetidin-3-carboxylic acid methyl ester (Oakwood Products, Inc.: Code No. W07L) (2.00 g, 7.16 mmol) was added dropwise over 10 minutes under ice cooling and stirring, and the reaction mixture was stirred for 3.5 hours. While the reaction mixture was stirred again under ice cooling, water (1.14 mL), a 4N-aqueous solution of sodium hydroxide (1.14 mL) and water (4.50 mL) were added to the reaction liquor, and the mixture was stirred for 20 minutes. Precipitated insoluble matter was removed through separation by filtration, and the obtained mother liquor was concentrated under reduced pressure to obtain the title compound (1.97 g, over yield) as an oily matter.

後処理

  1. stirringthe reaction mixture was stirred for 3.5 hours
  2. stirringWhile the reaction mixture was stirred again under ice cooling
  3. stirringthe mixture was stirred for 20 minutes
  4. customPrecipitated insoluble matter was removed through separation by filtration
  5. concentrationthe obtained mother liquor was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-87cecb4c941d4d2a8bcb8345b41b0ae2
出典データセット
uspto-grants-2012_03
特許番号
US08129366B2

反応ノート

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