ChemicalBook CAS DataBase List Cyclopropanecarboxylic acid, 1-[[(phenylMethoxy)carbonyl]aMino]-, Methyl ester

Cyclopropanecarboxylic acid, 1-[[(phenylMethoxy)carbonyl]aMino]-, Methyl ester synthesis

6synthesis methods

Product Name:Cyclopropanecarboxylic acid, 1-[[(phenylMethoxy)carbonyl]aMino]-, Methyl ester
CAS Number:84677-05-4
Molecular formula:C13H15NO4
Molecular Weight:249.26

Butanoic acid, 4-bromo-2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (2S)-

15159-67-8
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100-39-0
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Cyclopropanecarboxylic acid, 1-[[(phenylMethoxy)carbonyl]aMino]-, Methyl ester

84677-05-4
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$97.00/1g

Yield:84677-05-4 76%

Reaction Conditions:

with lithium hexamethyldisilazane in tetrahydrofuran at 0;

Steps:

Benzyl 1-(methoxycarbonyl)cyclopropylcarbamate (7).

Carbamate 4 (55 mg, 0.17 mmol) in THF (4 mL) at 0oC, LiN(SiMe3)2 (0.17 mL, 1 equiv) and benzyl bromide (30 mg, 0.17 mmol) were reacted and worked up according to procedure 6.8. The crude product was obtained as white solid (100 mg). Analysis of the crude solid by 1H NMR spectroscopy showed the formation of cyclopropane 7 in the presence of benzyl alcohol and LiN(SiMe3)2. Purification by silica gel chromatography (ethyl acetate: hexane: triethylamine; 29:70:1) gave pure cyclopropane 7 (32 mg, 76%) as a white powder. The 1H NMR spectrum was consistent with the values reported in the literature.^3,41H NMR (200 MHz, CDCl3) : δ 1.21 (m, 2H, 1 x H2 and 1 x H3), 1.56 (m, 2H, 1 x H2 and 1 x H3), 3.69 (s, 3H, OCH3), 5.13 (s, 2H, CH2C6H5), 5.34 (brs, 1H, Wh/2 = 6 Hz, NH), 7.35 (5H, m, C6H5).

References:

Loughlin, Wendy A.;Schweiker, Stephanie S.;Jenkins, Ian D.;Henderson, Luke C. [Tetrahedron,2013,vol. 69,# 5,p. 1576 - 1582] Location in patent:supporting information

72784-43-1 Synthesis