Reaktion #660030

Reaktionsgleichung

lithium aluminum hydride

3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]benzoic acid ethyl ester

lithium aluminum hydride

→

{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}methanol

Lösungsmittel

tetrahydrofurane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationhydrolyzed with water (178 μL), 5% sodium hydroxide (178 μL) and water (535 μL), filtered through a pad of clarcel
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   SonstigeThe residue is purified over silica gel (dichloromethane/methanol/ammonia 95/5/0.5)

Vorschrift

A solution of 3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]benzoic acid ethyl ester (0.55 g, example 206) in tetrahydrofurane (10 mL) is treated with lithium aluminum hydride (76 mg) at room temperature for 1 h. Two other additions of lithium aluminum hydride (76 mg each) allow a complete conversion. The mixture is then hydrolyzed with water (178 μL), 5% sodium hydroxide (178 μL) and water (535 μL), filtered through a pad of clarcel and concentrated under reduced pressure. The residue is purified over silica gel (dichloromethane/methanol/ammonia 95/5/0.5) to afford {3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}methanol which is then converted into its oxalate salt in acetone to give {3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}methanol, oxalate.

Quelle