Related Products of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, its 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.
Step 1; 4-(l-terf-Butoxycarbonyl-cyclopropyl)-4-hydroxy-piperidine-l-carboxylic acid benzyl ester: To a cooled (-780C) solution of 2.OM lithium dsopropylamide in heptane/ THF/ ethylbenzene (27.4 mL, 54.8 mmol) was added cyclopropanecarboxylic acid terf-butyl ester (7.08 g, 49.8 mmol) in THF (35 mL). After stirring at -780C for 1 h, a solution of 4-oxo-piperidine-l- carboxylic acid benzyl ester (11.6 g, 49.8 mmol) in THF (50 mL) was added. The reaction mixture was stirred at -780C for 3 h then warmed to room temperature. After stirring at ambient temperature for 16 h, the mixture was quenched with saturated aqueous solution of NH4Cl (150 mL) and extracted with EtOAc (150 mL x 3). The combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc in Hexane) to yield 4-(l-tert-butoxycarbonyl- cyclopropyl)-4-hydroxy-piperidine-l-carboxylic acid benzyl ester (8.07 g, 43%). 1H NMR (400 MHz, CDCl3) delta 7.36-7.28 (m, 5H), 5.11 (s, 2H), 4.50 (s, IH), 4.00 (bis, 2H), 3.20 (brs, 2H), 1.72- 1.64 (m, 2H), 1.42 (s, 9H), 1.40-1.30 (m, 2H), 1.10 (dd, J=7.0 and 2.4 Hz, 2H), 0.88 (dd, J=7.0 and 2.4 Hz, 2H).
The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; H. LUNDBECK A/S; PETERSON, John; CHEN, Chien-an; CHEN, Bin; WU, Lingyun; SABIO, Michael; WO2010/53861; (2010); A2;,
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