1,1-Dimethylethyl 4-oxo-2-(trifluoromethyl)-1-piperidinecarboxylate

To a solution of 2-(benzo[djthiazol-2-yl)acetonitrile (300 mg, 1.72 mmol) in ethanol (10 mL) was added NaBH4 (76 mg; 2 mmol; 2 eq.) was added at -10°C to a solution of 1-Boc-2- trifluoromethyl- piperidin-4-one (Small Molecules inc.) (267 mg; 1 mmol; 1 eq.) in MeOH (8 mL) and the reaction mixture was stirred at -10°C for 1 hour. Sat. aq. NH4CI (3 mL) was added and the resulting mixture was allowed to return to room temperature. The MeOH was evaporated in vacuo and the resulting aqueous layer extracted with DCM (4x). The combined organics were washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (269 mg, 100percent) as a colourless oil. 1H NMR (CDCI3) delta 4.74 (br s, 1 H), 4.19-3.93 (m, 2H), 3.42-3.17 (m, 1H), 2.14-1.90 (m, 2H), 1.90-1.52 (m, 3H), 1.52-1.37 (m, 9H).Sodium borohydride (71 mg, 1.87 mmol) was added at -10 °C to a solution of 1-boc-2-trifluoromethyl-piperidin-4-one (250 mg, 0.94 mmol) in MeOH (8 mL) and the reaction stirred at -10 °C for lh. Sat. aq. NH4CI (3 mL) was added, and the resulting mixture allowed to warm to RT. The MeOH was removed under reduced pressure, and the resulting aqueous layer extracted with DCM (4 x 5 mL). Thecombined organics were washed with brine, dried over Mg504, filtered and concentrated under reduced pressure to afford 247.6 mg (98percent yield) of the title compound as colourless oil.1H NMR (250 MHz, Chloroform-d): 6 [ppm] 4.84 - 4.62 (m, 1H), 4.15 - 3.95 (m, 2H), 3.39- 3.18 (m, 1H), 2.10-2.00 (m, 1H), 1.91 - 1.57 (m, 3H), 1.47 (5, 9H).

Molecular Weight:267.24
XLogP3:1.7
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:267.10822786
Monoisotopic Mass:267.10822786
Topological Polar Surface Area:46.6
Heavy Atom Count:18
Complexity:346
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes