1-BOC-3-[(1,1-DIMETHYLETHYL)DIMETHYLSILYLOXYMETHYL]-PIPERIDIN-4-ONE

Oxalyl chloride (5.71 g, 0.0450 mol) was dissolved in dry CH[00192j Step 1: tert-butyl 3- [[tert-butyl(dimethyl)silylj oxymethyll - 4-oxo-piperidine- 1-carboxylate [00195j To a 250 mL round bottom flask containing crude tert-butyl 3- [[tert-butyl(dimethyl)silyl]oxymethyl] -4-hydroxy-piperidine- 1 -carboxylate (2.4 g) was added DCM (24 mL) and sodium bicarbonate (2.0 g, 20.4 mmol). The reaction mixture was cooled to 0 °C for 5 mm and Dess-Martin periodane (3.6 g, 8.5 mmol) was added. The reaction mixture was stirred for 3 h while warming to rt. The reaction mixture wasfiltered and concentrated under reduced pressure to dryness. The crude product was purified via silica gel chromatography (0-50percent) DCM:ethyl acetate to provide tertbutyl 3- [[tert-butyl(dimethyl)silyl]oxymethyl] -4-oxo-piperidine- 1 -carboxylate (1.7 g, 71percent) as a clear yellow oil. ESI-MS mlz calc. 343.5, found 344.4 (M+1) Retention time: 2.47 mm (3 mm run).To a stirred solution of teri-butyl 3-[[teri-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-piperidine-l- carboxylate (1800 mg; 4.40 mmol) in dichloromethane (15 mL) was added Dess-Martin periodinane (3800 mg; 8.80 mmol) at 0 °C. After stirring for 2 hours at 15 °C, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; petroleum ether:ethyl acetate; 4:1 ; v/v) to afford teri-butyl 3-[[teri-butyl(dimethyl)silyl]oxymethyl]-4-oxo- piperidine-1 -carboxylate (1100 mg) as a colorless oil. MS m/z (+ESI): 344.1 [M+H]

Molecular Weight:343.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:343.21788507
Monoisotopic Mass:343.21788507
Topological Polar Surface Area:55.8
Heavy Atom Count:23
Complexity:449
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes