tert-Butyl4-(oxan-4-ylamino)piperidine-1-carboxylate(WXC08109) synthesis

Yield:710977-70-1 88%

Reaction Conditions:

Stage #1: 4-aminotetrahydropyran;N-tert-butyloxycarbonylpiperidin-4-one in 1,2-dichloro-ethane at 20; for 0.166667 h;
Stage #2: with sodium tris(acetoxy)borohydride;acetic acid in 1,2-dichloro-ethane at 20;

Steps:

97 Synthesis of Int-97-3

A mixture of Int-97-1 (1.37 g, 6.89 mmol) and tetrahydro-2H-pyran-4- amine Int-97-2 (1.395 g, 13.79 mmol) in 1,2-dichloroethane (20 mL) was stirred at RT for 10 min. To the mixture NaBH(OAc)₃ (2.92 g, 3.79 mmol) and AcOH (0.78 mL, 13.79 mmol)) were added. The reaction mixture was stirred at RT overnight. The solvent was evaporated under reduced pressure, and the residue was partitioned between saturated aqueous solution of Na₂CO₃ and EtOAc. The organic phase was separated, and the aqueous layer was extracted with EtOAc (2 x 40 mL). The combined organic phase was dried over Na₂SO₄ and evaporated under reduced pressure. The product was purified by column chromatography (CH₂Cl₂: MeOH = 97:3) to afford Int- 97-3 as yellow oil (1.716 g, 88% yield). LC-MS: (M+1) m/z = 285.

References:

WO2018/170492,2018,A1 Location in patent:Page/Page column 133; 134