HCID 66735004, compound → HCID 46937587, compound

HRID 1963497Notes

Reaction equation

HRID 1963497 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 66735004HCID 66735004, compound

Product 1

HCID 46937587HCID 46937587, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

(2S,4S)-Methyl 2-cyclohexyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (79 mg, 0.26 mmol) was stirred in HBr (33% in AcOH) overnight. Evaporation of solvents and the residue purified by preparative HPLC (Instrument: FractionLynx I, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm.) to yield 5-((2S,4S)-2-cyclohexylpiperidin-4-yl)isoxazol-3(2H)-one 22 mg (35%). 1H NMR (400 MHz, cd3od) δ 1.00-1.39 (m, 5H), 1.51-1.64 (m, 1H), 1.64-1.93 (m, 6H), 1.96-2.11 (m, 1H), 2.15-2.25 (m, 1H), 2.26-2.35 (m, 1H), 2.92-3.02 (m, 1H), 3.03-3.16 (m, 1H), 3.22-3.33 (m, 2H), 5.57 (s, 1H). HRMS Calcd for [C14H22N2O2+H]+: 251.1760. Found: 251.1754.

Workup

  1. customEvaporation of solvents
  2. customthe residue purified by preparative HPLC (Instrument

Sources & evidence

ORD record
ord-d628ac49404644f3bd4061813a49b961
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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