4-(3-Hydroxyazetidin-1-yl)benzoic acid synthesis
- Product Name:4-(3-Hydroxyazetidin-1-yl)benzoic acid
- CAS Number:1416784-71-8
- Molecular formula:C10H11NO3
- Molecular Weight:193.2
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Yield:-
Reaction Conditions:
Stage #1: ethyl 4-(3-hydroxyazetidine-1-yl)benzoatewith lithium hydroxide monohydrate in tetrahydrofuran;methanol;water at 40;
Stage #2: with hydrogenchloride in water; pH=7;
Steps:
3.2 4-(3-Hydroxyazetidin-1-yl)benzoic acid
A mixture of 1-[4-(3-hydroxyazetidin-1-yl)phenyl]-2-methoxyethanone (1.33 g, 6.00 mmol) and lithium hydroxide monohydrate (504 mg, 12.0 mmol) in water (4 mL), methanol (3 mL) and THF (6 mL) was stirred at 40° C. overnight. The mixture was neutralized with 3 N HCl aqueous solution (4 mL) to pH about 7, extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product (1.10 g, 94.9%) which was directly used in the next step without further purification. LCMS cacld. for C10H12NO3 (M+1)+: m/z=194.1. Found: 194.1.
References:
US2014/343030,2014,A1 Location in patent:Paragraph 0438; 0440
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