Tetrahydrofuran → (1-Benzhydrylazetidin-3-yl)methanol
Reaction equation
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]=1Participants
Procedure
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.
Workup
- stirringthe reaction mixture was stirred for 3.5 hours
- stirringWhile the reaction mixture was stirred again under ice cooling
- stirringthe mixture was stirred for 20 minutes
- customPrecipitated insoluble matter was removed through separation by filtration
- concentrationthe obtained mother liquor was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-87cecb4c941d4d2a8bcb8345b41b0ae2
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129366B2
Reaction notes
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