Methyl 1-aminocyclopropanecarboxylate

To MeOH (50 mL) was added SOClStep 6: 1-Aminocyclopropanecarboxylic acid methyl ester (0598) 1-Aminocyclopropanecarboxylic acid (202 mg, 2 mmol) in methanol (4 mL) was cooled to −10° C. and to this was added dropwise thionyl chloride (581 μL, 8 mmol). The mixture was allowed to warm and was then refluxed for 2 hours. Solvents were evaporated and the residue redissolved in boiling alcohol. To the cooled solution was added diethyl ether to the point of turbidity when the mixture was refridgerated for 2 days. The resulting precipitates afford the product (223 mg, 67percent) that was used in Step 7.The method of claim 1, wherein the compound utilized to treat the disorder is selected from the group consisting of 1-aminocyclopropanecarboxylic acid, The method of claim 1, wherein the neuropsychopharmacological disorder is an epilepsy or anxiety disorder, and the compound utilized to treat the disorder is selected from the group consisting of 1-aminocyclopropanecarboxylic acid, The method of claim 1, wherein the neuropsychopharmacological disorder is epilepsy, and the compound utilized to treat the disorder is selected from the group consisting of 1-aminocyclopropanecarboxylic acid, The method of claim 5, wherein the compound is: 1-aminocyclopropanecarboxylic acid, A solution of phenyl {4-[(3-chloro-1 -{[2-(trimethylsilyl)ethoxy]methyl}-1 H-pyrrolo[2, 3-b]pyridin-4- yl)oxy]-3, 5-difluorophenyl}carbamate (1 .00 g, 1 .83 mmol, intermediate 44) and methyl 1 - aminocyclopropanecarboxylate (253 mg, 2.20 mmol, CAS No. [72784-43-1 ]) in DMF (4.9 mL) was heated to 90C overnight. The reaction mixture was cooled, diluted with ethyl acetate and water was added. The layers were separated and the aqueous phase extracted twice with ethyl acetate. The combined organic layers were washed with Brine, dried over sodium sulfate, and evaporated in vacuo to afford the crude product. The crude product was purified by flash column chromatography (50g Si-snap colum, hexane/ethylacetate / 10% -> 60% ethylacetate) to obtain 650 mg (56 % yield) of the title compound. LC-MS (method 2): Rt = 1 .49 min; MS (ESIpos): m/z = 567 [M+H]+ 1H NMR (400 MHz, DMSO-d6) delta ppm -0.10 (s, 9 H), 0.79 - 0.85 (m, 2 H), 1 .10 - 1 .15 (m, 2 H), 1 .39 - 1 .44 (m, 2 H), 3.50 - 3.57 (m, 2 H), 3.62 (s, 3 H), 5.60 (s, 2 H), 6.44 (d, 1 H), 7.19 (s, 1 H), 7.42 (br d, 2 H), 7.83 (s, 1 H), 8.17 (d, 1 H), 9.10 (br s, 1 H)methyl 1-aminocyclopropylcarboxylate (800mg, 6.96mmol) and 20mLtetrahydrofuran were added into a 100mL three-neck flask, the mixture was cooled to 0C under argon atmosphere, then a solution of lithium aluminum hydride in tetrahydrofuran (15mL, 7.5mmol) was added dropwise. After completionof the addition, the reaction solution was stirred at room temperature for 18 hours. After completion of the reaction, thereaction solution was quenched, filtered through celite, dried over anhydrous sodium sulfate and concentrated to give800mg crude product, which was used directly in the next step.

Molecular Weight:115.13
XLogP3:-0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:115.063328530
Monoisotopic Mass:115.063328530
Topological Polar Surface Area:52.3
Heavy Atom Count:8
Complexity:118
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes