1-Benzyl-5-(hydroxyMethyl)piperidin-2-one

(±) Compound 4 (5.23 g, 23.85 mmol) was dissolved in anhydrous THF (35 mL) and cooled to 0 °C. LiBH4 (1.04 g, 47.70 mmol) was added and the solution was allowed to warm to room temperature and stirred overnight. The reaction was quenched at 0 °C with water (20 mL) and then with 10percent HC1. The organic layer was separated and the aqueous layer was extracted with EtOAc (4 x 20 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The crude oil was purified by silica gel column chromatography (cyclohexane/EtOAc, 60:40) to give (±) Compound 5(4.03 g, 77percent yield) as a clear oil. (Rf= 0.11, cyclohexane/EtOAc, 50:50). H (600 IVIFlz; CDC13) 7.33-7.18 (5H, m, PhH), 4.59 (1H, d, J 14.6, PhCH2), 4.53 (1H, d, J 14.6, PhCH2), 3.53 (1H, dd, J 10.7 and 5.6, CH2OH), 3.44 (1H, dd, J= 10.7 and 7.2, CH2OH), 3.30(1H, ddd, J= 12.2, 5.2 and 1.5, NCH2), 2.99 (1H, dd, J= 12.2 and 10.1, NCH2), 2.92 (1H, br s, OH), 2.51 (1H, ddd, J= 17.8, 5.8 and 3.4, C=OCH2), 2.39 (ddd, J= 17.8, 11.3 and 6.5, C=OCH2), 2.04-1.95 (1H, m, OHCH2CI]), 1.89-1.82 (1H, m, C=OCH2CH2), 1.54 — 1.46 (1H, m, C=OCH2CH2); C (151 MHz; CDC13) 170.0, 137.0, 128.5, 127.9, 127.3, 64.3, 50.3, 49.8, 36.4, 31.1, 23.8; m/z (ES) 220.1329 (M+W C13H18N02 requires 220.1338).To a solution of 12-S3 (3.2 g, 13.0 mmol) in THF (45 mL) was added LiBH4 (566 mg, 26.0 mmol) at 0 °C. The reaction mixture was stirred under an atmosphere of nitrogen at room temperature overnight. The reactionmixture was quenched with water and extracted with EtOAc (50 mL). The organic phase was washed with brine, dried over anhydrous Na2SO4, and concentrated. The remaining residue was purified by column chromatography on silica gel (eluted with DCMIMeOH = 50:1) to afford the title compound (2.2 g, 77.3percent yield) as a yellow oil. LC/MS (ESI) m/z: 220 (M+H).General procedure: The alkene (1mmol) and catalyst (at the specified catalytic loading) were added to a small glass hydrogenation vial. A suba seal was attached and the contents were flushed with nitrogen for 10min before the dry solvent (as specified) was added. The suba seal was removed and the vial was quickly placed into the hydrogenation apparatus. The hydrogenator was filled with hydrogen to the appropriate pressure before the pressure was nearly completely released. The hydrogenator was then filled again with hydrogen and the pressure was released. This fill release cycle carried out for a total of three times to ensure the vessel was sufficiently charged with hydrogen at the stated pressure. A magnetic stirrer box was placed under the hydrogenator to enable stirring for the specified time before the hydrogen was carefully released and the apparatus was disassembled. Following concentration under reduced pressure, the product was obtained, following purified by column chromatography (where applicable).

Molecular Weight:219.28
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:219.125928785
Monoisotopic Mass:219.125928785
Topological Polar Surface Area:40.5
Heavy Atom Count:16
Complexity:236
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes