ChemicalBook CAS DataBase List 1S,2R)-cis-2-Methoxycarbonyl-cyclopentane-1-carboxylic acid

1S,2R)-cis-2-Methoxycarbonyl-cyclopentane-1-carboxylic acid synthesis

6synthesis methods

Product Name:1S,2R)-cis-2-Methoxycarbonyl-cyclopentane-1-carboxylic acid
CAS Number:88315-64-4
Molecular formula:C8H12O4
Molecular Weight:172.18

67-56-1 Synthesis

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1-CYCLOPENTENE-1,2-DICARBOXYLIC ANHYDRIDE

3205-94-5
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1S,2R)-cis-2-Methoxycarbonyl-cyclopentane-1-carboxylic acid

88315-64-4
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Yield:88315-64-4 100%

Reaction Conditions:

with quinine in tetrachloromethane;toluene at -55; for 36 h;

Steps:

22.a

15,2R)-2-(Methoxycarbonyl)cyclopentanecarboxylic acid was prepared as described in /. Org. Chem. 2000, 65, 6984-6991. Tetrahydro-cyclopenta[c]furan-l,3- dione (5.0 g, 35.7 mmol) was dissolved in a 1:1 mixture of toluene and carbon tetrachloride (720 mL). The mixture was cooled to -55 ⁰C under a nitrogen atmosphere, and then quinine (12.7 g, 39.3 mmol) was added. A solution of methanol (4.33 mL, 107 mmol) in toluene-carbon tetrachloride (1:1, 30 mL) was slowly added via an addition funnel. The suspension was stirred at -55 ⁰C for 36 h, and then allowed to warm to 25 ⁰C. The mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (400 mL), washed with 1.0 M aqueous hydrochloric acid solution (2 x 400 mL) and saturated aqueous brine solution, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to afford the desired product, (lS,2R)-2-(methoxycarbonyl)cyclopentanecarboxylic acid (6.2 g, 35.7 mmol, quantitative), as a clear oil. ¹H NMR (400 MHz, CD₃OD) δ: 1.67 (IH, m), 1.84 (IH, m), 1.99 (4H, m), 3.08 (2H, m), 3.63 (3H, s).

References:

WO2008/73982,2008,A2 Location in patent:Page/Page column 130-131

67-56-1 Synthesis

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