Sodium Sulfate → 3-Pentyl-3-phenylazetidine
Reaction equation
[C:1]([C:3]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:4]OS(C1C=CC(C)=CC=1)(=O)=O)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].S([O-])([O-])(=O)=O.[Na+].[Na+].O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:16]([C:3]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:1][NH:2][CH2:4]1)[CH2:17][CH2:18][CH2:19][CH3:20]Participants
Procedure
To a solution containing 5.26 g (14.1 mmol) of toluene-4-sulfonic acid 2-cyano-2-phenylheptyl ester in 25 mL of THF under nitrogen are added cautiously 600 mg (15.5 mmol) of LiAlH4 powder. The reaction medium is stirred for 1 hour at room temperature and then treated with a sodium sulfate paste (hot water+Na2SO4). After stirring for 30 minutes at room temperature, the salts formed are filtered off and the filtrate is evaporated under reduced pressure. The residue is taken up in dichloromethane and washed with aqueous 1N sodium hydroxide solution. The organic phase is dried over sodium sulfate, filtered and evaporated under reduced pressure. 2.90 g of a colourless oil are obtained and used in the following step without further purification.
Workup
- stirringAfter stirring for 30 minutes at room temperature
- customthe salts formed
- filtrationare filtered off
- customthe filtrate is evaporated under reduced pressure
- washwashed with aqueous 1N sodium hydroxide solution
- dry with materialThe organic phase is dried over sodium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b953abbd11b24a76b0c4eccccfbf6066
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877968B2
Reaction notes
Loading…