HCID 68503455, compound → HCID 46937586, compound

HRID 1963494Notes

Reaction equation

HRID 1963494 reaction equation
[CH:1]1([C@H:7]2[CH2:12][C@@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][N:8]2C(OC)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Br>[CH:1]1([C@H:7]2[CH2:12][C@@H:11]([C:13]3[O:17][NH:16][C:15](=[O:18])[CH:14]=3)[CH2:10][CH2:9][NH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 68503455HCID 68503455, compound

Product 1

HCID 46937586HCID 46937586, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

(2R,4S)-Methyl 2-cyclohexyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.427 g, 1.38 mmol) was stirred in HBr (33% in AcOH) overnight (19 hours). Evaporation of solvents and the residue purified by preparative HPLC (Instrument: FractionLynx I, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2R,4S)-2-cyclohexylpiperidin-4-yl)isoxazol-3(2H)-one (228 mg, 66%). 1H NMR (400 MHz, cd3od) δ 1.05-1.42 (m, 5H), 1.49-1.66 (m, 2H), 1.67-1.91 (m, 6H), 2.17-2.26 (m, 1H), 2.26-2.35 (m, 1H), 2.97-3.19 (m, 3H), 3.43-3.52 (m, 1H), 5.70 (s, 1H), 8.51 (s, 1H). HRMS Calcd for [C14H22N2O2+H]+: 251.1760. Found: 251.1750.

Workup

  1. customEvaporation of solvents
  2. customthe residue purified by preparative HPLC (Instrument: FractionLynx I, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm)

Sources & evidence

ORD record
ord-7a7303f552d94033906ceb738cff7a11
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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