(2S,4S)-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate → 5-((2S,4S)-2-(3,3-Dimethylbutyl)piperidin-4-yl)-isoxazol-3(2H)-one

HRID 1963534Notes

Reaction equation

HRID 1963534 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][C@H:5]1[CH2:10][C@@H:9]([C:11]2[O:15][NH:14][C:13](=[O:16])[CH:12]=2)[CH2:8][CH2:7][N:6]1C(OC)=O>Br>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][CH2:4][C@H:5]1[CH2:10][C@@H:9]([C:11]2[O:15][NH:14][C:13](=[O:16])[CH:12]=2)[CH2:8][CH2:7][NH:6]1

Participants

3

Reactant 1

HCID 68501685(2S,4S)-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate

Product 1

HCID 469376995-((2S,4S)-2-(3,3-Dimethylbutyl)piperidin-4-yl)-isoxazol-3(2H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

(2S,4S)-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (341 mg, 1.1 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 20 mL) and the mixture was stirred at room temperature for 24 h. The solvent was evaporated and the compound was purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm) using a gradient of 5-30% Acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 15 minutes with a flow of 100 mL/min. 5-((2S,4S)-2-(3,3-Dimethylbutyl)piperidin-4-yl)-isoxazol-3(2H)-one (235 mg, 85%) was isolated. 1H NMR (600 MHz, cd3od) δ 0.90 (s, 9H), 1.22-1.34 (m, 2H), 1.43-1.78 (m, 4H), 2.10 (d, 1H), 2.22 (d, 1H), 2.85-2.94 (m, 1H), 2.98-3.07 (m, 2H), 3.40 (d, 1H), 5.46 (s, 1H). HRMS Calculated for [C14H24N2O2+H]+: 253.1916. Found: 253.1898

Workup

  1. customThe solvent was evaporated
  2. customthe compound was purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm)
  3. custombuffer over 15 minutes

Sources & evidence

ORD record
ord-6ad5b61553b041c882b5d0b736e96a1f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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