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

HRID 1091288노트

반응식

HRID 1091288 반응식
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

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 14798Sodium HydroxideHCID 2759842Methyl 1-(diphenylmethyl)azetidine-3-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 2758715(1-Benzhydrylazetidin-3-yl)methanol수율 108.6%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87cecb4c941d4d2a8bcb8345b41b0ae2
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129366B2

반응 노트

불러오는 중…