HCID 68501730, compound → HCID 66732653, compound

HRID 1963586Notes

Reaction equation

HRID 1963586 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][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)=[CH:4][CH:3]=1>Br>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][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)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68501730HCID 68501730, compound

Product 1

HCID 66732653HCID 66732653, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

(2R,4S)-Methyl 2-(4-chlorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (253 mg, 0.72 mmol) was stirred in HBr (33% in AcOH) overnight (24 hours). Evaporation of solvents and the residue was purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm) using a gradient of 5% to 45% Acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 20 minutes with a flow of 100 mL/min. 5-((2R,4S)-2-(4-chlorobenzyl)piperidin-4-yl)isoxazol-3(2H)-one (150 mg, 71%) was isolated. 1H NMR (400 MHz, cd3od) δ 1.37-1.50 (m, 1H), 1.61-1.77 (m, 1H), 2.01-2.13 (m, 2H), 2.78-2.98 (m, 4H), 3.18-3.28 (m, 1H), 3.28-3.36 (m, 1H), 5.51 (s, 1H), 7.24 (d, 2H), 7.34 (d, 2H). HRMS Calcd for [C15H17ClN2O2+H]+: 293.1057. Found: 293.1043.

Workup

  1. customEvaporation of solvents
  2. customthe residue was purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm)
  3. custombuffer over 20 minutes

Sources & evidence

ORD record
ord-2ce31b711af145d6ba18e8a65a671ae2
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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