HCID 131730372, compound → 5-[(2S,4S)-2-(2-Methylpropyl)-4-piperidinyl]-3(2H)-isoxazolone

HRID 1963349Notes

Reaction equation

HRID 1963349 reaction equation
[CH2:1]([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)[CH:2]([CH3:4])[CH3:3]>Br>[CH2:1]([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)[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 131730372HCID 131730372, compound

Product 1

HCID 469380415-[(2S,4S)-2-(2-Methylpropyl)-4-piperidinyl]-3(2H)-isoxazoloneYield 69.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Racemic cis-methyl 2-isobutyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.29 g, 1.03 mmol) was stirred in HBr (12 mL, 33% in HOAc) for 24 h. The volatiles were concentrated and the residue purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm) using a gradient of 0-25% acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 10 minutes with a flow of 100 mL/min. The title compound (160 mg) was isolated. 1H NMR (600 MHz, d2o) δ 0.79 (2 d, 6H), 1.34-1.51 (m, 3H), 1.54-1.72 (m, 2H), 2.13 (m, 1H), 2.25 (m, 1H), 2.99 (m, 2H), 3.21 (m, 1H), 3.38 (m, 1H), 5.61 (s, 1H).

Workup

  1. concentrationThe volatiles were concentrated
  2. customthe residue purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm)
  3. custombuffer over 10 minutes

Sources & evidence

ORD record
ord-0dc2ad42b88345979a367d6da49901d3
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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