Hydrogen Bromide → HCID 46937644, compound

HRID 1963522Notes

Reaction equation

HRID 1963522 reaction equation
[F:1][C:2]1([F:25])[CH2:7][CH2:6][CH:5]([CH2:8][C@@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2C(OC)=O)[CH2:4][CH2:3]1.Br>>[F:25][C:2]1([F:1])[CH2:7][CH2:6][CH:5]([CH2:8][C@@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][NH:10]2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 66732723HCID 66732723, compound

Product 1

HCID 46937644HCID 46937644, compoundYield 66%

Procedure

(2R,4R)-Methyl 2-((4,4-difluorocyclohexyl)methyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (0.752 g, 2.10 mmol) (from example 89, step 3) was dissolved in hydrogen bromide (33% in acetic acid, 16.54 mL, 94.42 mmol) and the mixture stirred at room temperature overnight. The solvent was evaporated and the residue 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,4R)-2-((4,4-difluorocyclohexyl)methyl)piperidin-4-yl)isoxazol-3(2H)-one (415 mg, 66%). HRMS Calculated for [C15H22F2N2O2+H]+: 301.1728. Found: 301.1741

Workup

  1. customThe solvent was evaporated
  2. customthe residue 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-0be156191fd44c83bd63f1429fa268c0
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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