Cyclopropanecarboxaldehyde, 2-phenyl-, (1S,2R)- (9CI) synthesis

5synthesis methods

Product Name:Cyclopropanecarboxaldehyde, 2-phenyl-, (1S,2R)- (9CI)
CAS Number:186183-64-2
Molecular formula:C10H10O
Molecular Weight:146.19

29667-46-7
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Cyclopropanecarboxaldehyde, 2-phenyl-, (1S,2R)- (9CI)

186183-64-2
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Yield:186183-64-2 75%

Reaction Conditions:

with 4-methyl-2-morpholinone;tetra-n-propylammonium perruthenate. in dichloromethane at 20; for 3 h;Inert atmosphere;

Steps:

1.4 Step 4

To a solution of compound a4 (1.50g, 10.lmmol)dichioromethane (20m1) were added sequencially molecular sieve4A (5.Og), N-methylmorpholine oxide (2.95g, 25.3mmol) and tetrapropylammonium perruthenate (354mg, l.Olmmol) under argon atmosphere, and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was filtered overcelite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel, chromatography (hexane:ethyl acetate =5:1) to yield compound a5 (l.llg, 7.6lmmol,75%) as a colorless liquid.NMR data was consistent with the literature values.

References:

WO2014/10748,2014,A1 Location in patent:Paragraph 0187; 0191