Electric Literature of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
EXAMPLE 61 120N-(5-(l-piperazinyl)-2-pyridinyl)spiro[cyclopentane-l,9′- pyrido [4′,3′ :3,4] cyclopenta[l,2-d] pyrimidin]-2′-amine 1212-(3-Bromo-4-pyridinyl)-l-cyclopentylethanone (121) Under a nitrogen atmosphere LiHMDS (LOM solution in tetrahydrofuran, 49.6 ml, 49.6 mmol) was added to a solution of methyl cyclopentanecarboxylate (3.630 g, 28.3 mmol) and 3-bromo-4-methylpyridine (2.62 ml, 23.6 mmol) in 10ml of anhydrous THF over a period of 5min at -780C. AfterlOmin the solution was allowed to warm to 2O0C and stirred for 2hours. The solution was then cooled in ice water, before the pH was adjusted to 4.5 with 25% citric acid. After extraction with DCM the organic layer was dried over Na2SO4 and then concentrated to afford 2-(3-bromo-4-pyridinyl)-l-cyclopentylethanone (121) (6.86g, crude). 1H NMR (500 MHz, DMSO-d6) delta 8.68 (IH, s), 8.48 (IH, d, J = 4.9Hz), 7.37 (H, d, J = 4.9 Hz), 4.07 (2H, s), 3.08 (IH, ddd, Jl = 16.1 Hz, J2 = 7.3 Hz, J3 = 1.2 Hz), 1.80- 1.85 (2H, m), 1.72-1.77 (2H, m), 1.55-1.59 (4H, m); LCMS-ESI (POS), M/Z, M+l : Found 268.0
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl cyclopentanecarboxylate, its application will become more common.
Reference:
Patent; AMGEN INC.; WO2009/126584; (2009); A1;,
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