6,7-DIHYDRO-5H-1-PYRIDIN-5-ONE

A solution of 0.883 mg of Mn (OTf) 2 (0.5 molpercent), 60 mg of 2, 3-cyclopentenopyridine, 0.35 g of 65percent aqueous TBHP and 2.5 ml of water was added successively to a 25 mL round bottom flask, in the air at room temperature for 24 hours, the reaction solution was extracted with 3 x 5 mL of ethyl acetate, the ethyl acetate layer was collected, dried over anhydrous sodium sulfate, filtered and the ethyl acetate was distilled off, using petroleum ether and ethyl acetate in a volume ratio of 5: 1 as eluent, the product of 6, 7-dihydro-5H-cyclopenta [b] pyridin-5-one 60.5 mg was obtained as a pale yellow solid in a yield of 91percent by silica gel column chromatography.General procedure: A 15‐mL RBF was charged with substrate (0.5 mmol), MnOx‐N(at)C catalyst (1 mg, pyrolysis at 600 °C) and TBHP (1.5mmol, 65percent in H2O). The flask was then sealed, and the mixturewas heated at 60 °C for 12 h. The reaction was cooled to roomtemperature and diluted with ethyl acetate (4 mL), before beingcentrifuged at 10000 r/min for 1 min to separate the catalyst.The supernatant was removed and the catalyst waswashed with ethyl acetate (5 × 4 mL). The supernatant wassubsequently combined the ethyl acetate wash solutions andevaporated to dryness to give a residue, which was purified byflash column chromatography over silica gel (ethyl acetate/n‐hexane = 1:10, v/v).To a stirring solution of 6, 7-dihydro-5H-cyclopenta[b]pyridine SM1 (3.83 g, 32 mmol) in HOAc (20 mL) and conc.H2S04 (3.5 ml) was added a solution of Cr03 (6.7 g, 67.2mmol) in 10 mlof HOAc and 2 mL of H20. The temperature was kept below 10 °C during the addition. Afteraddition completed the resultant mixture was stirred at room temperature overnight. The mixture was then poured into crushed ice and treated with NH4OH to pH 11 and extracted with DCM. The organic phase was worked up and purified by silica gel column chromatography eluting with 50percent EtOAc/Hexane to afford compound 1(1.1 g, 35percent). LC-MS: m/z = 134.0[M+H]6, 7-Dihydro-[1]pyrindin-5-oneStep A 6, 7-dihydro-5H-cyclopenta[b]pyridin-5-one (24a)General procedure: To a stirred solution of ketone (1 equiv.) and (S)-2-methylpropane-2-sulfinamide (1 equiv.) in dry THF was added titanium (IV) ethoxide (1.8 equiv.). The resulting mixture was cautiously stirred at 100C for 2-3 h in a sealed tube. The reaction mixture was cooled to room temperature, diluted with brine and ethyl acetate. The resulting suspension was filtered through Celite and the filter cake was washed with ethyl acetate. The organic layer was separated and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography to afford the desired product.(S)-//-(6, 7-dihydro-5/-/-cyclopenta[b]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide 1H NMR: dH (400 MHz, DMSO-d6) 8.75 (1 H, dd, 6.4, 1.5), 8.09 - 8.06 (1 H, m), 7.44 - 7.40 (1 H, m), 3.20 - 3.13 (4H, m), 1.27 (9H, s).A 5 L 4-neck round bottom flask was charged

Molecular Weight:133.15
XLogP3:0.6
Hydrogen Bond Acceptor Count:2
Exact Mass:133.052763847
Monoisotopic Mass:133.052763847
Topological Polar Surface Area:30
Heavy Atom Count:10
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes