Hydrogen Bromide → HCID 46937584, compound

HRID 1963488Notes

Reaction equation

HRID 1963488 reaction equation
[O:1]=[C:2]1[CH:6]=[C:5]([C@H:7]2[CH2:12][CH2:11][N:10](C(OC)=O)[C@@H:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8]2)[O:4][NH:3]1.Br>>[C:17]1([C@H:9]2[CH2:8][C@@H:7]([C:5]3[O:4][NH:3][C:2](=[O:1])[CH:6]=3)[CH2:12][CH2:11][NH:10]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 68500601HCID 68500601, compound

Product 1

HCID 46937584HCID 46937584, compoundYield 61.1%

Procedure

(2R,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-phenylpiperidine-1-carboxylate (621 mg, 2.05 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 7 mL, 99.92 mmol) and the mixture stirred at room temperature for 24 h. The solvent was evaporated and the residue was purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2R,4S)-2-phenylpiperidin-4-yl)isoxazol-3(2H)-one (306 mg, 61%) (the isolated sample contained DMSO). 1H NMR (400 MHz, cd3od) δ 1.76-2.02 (m, 2H), 2.11-2.30 (m, 2H), 3.05-3.21 (m, 2H), 3.41-3.49 (m, 1H), 4.14 (dd, 1H), 5.56 (s, 1H), 7.27-7.48 (m, 5H). HRMS Calculated for [C14H16N2O2+H]+: 245.1290. Found: 245.1270

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm)

Sources & evidence

ORD record
ord-ef382ee1bc8e46c682e00635a2eb1fea
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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