HCID 68503570, compound → HCID 46938037, compound

HRID 1963347Notes

Reaction equation

HRID 1963347 reaction equation
[CH2:1]([C@H:8]1[CH2:13][C@@H:12]([C:14]2[O:18][NH:17][C:16](=[O:19])[CH:15]=2)[CH2:11][CH2:10][N:9]1C(OC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br>[CH2:1]([C@H:8]1[CH2:13][C@@H:12]([C:14]2[O:18][NH:17][C:16](=[O:19])[CH:15]=2)[CH2:11][CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 68503570HCID 68503570, compound

Product 1

HCID 46938037HCID 46938037, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

To (2R,4S)-methyl 2-benzyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.47 g) was added HBr (33% in HOAc, 10 mL) and the solution was stirred for 16 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 0-40% acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 15 minutes with a flow of 100 mL/minutes. The title compound was isolated (0.26 g, 29%): 1H NMR (600 MHz, dmso) δ 1.07 (m, 1H), 1.26-1.45 (m, 1H), 1.75 (m, 2H), 2.53 (m, 2H), 2.58-2.67 (m, 2H), 2.69 (m, 1H), 2.97 (m, 1H), 5.66 (s, 1H), 7.08-7.34 (m, 5H); [α]20D +67.8 (MeOH/H2O 1:1, c=1); HRMS Calculated for [C15H19N2O2]+: 259.1447. found: 259.1442.

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 15 minutes

Sources & evidence

ORD record
ord-94ae76fe8cb04a49a9dbca5187a90490
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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