Hydrogen Bromide → HCID 46938158, compound

HRID 1963354Notes

Reaction equation

HRID 1963354 reaction equation
Br.[CH:2]1([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)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>>[CH:2]1([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)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 68502462HCID 68502462, compound

Product 1

HCID 46938158HCID 46938158, compoundYield 69%

Procedure

HBr (33% in acetic acid) (7 mL) was added to a reaction flask containing (2R,4S)-methyl 2-(cyclohexylmethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.11 g, 0.34 mmol). The reaction was stirred vigorously overnight. The solvent was evaporated. Purification using preparative HPLC (pH=11, small column, sample dissolved in methanol/water (50/50), gradient 0-40, 20 minutes) gave the title compound (62 mg, yield 69%). 1H NMR (600 MHz, cd3od) δ 0.94 (s, 2H), 1.18 (s, 1H), 1.27 (s, 2H), 1.35-1.55 (m, 3H), 1.57-1.80 (m, 6H), 2.01 (s, 1H), 2.13 (s, 1H), 2.24 (s, 1H), 3.09 (s, 1H), 3.22 (s, 3H), 5.53 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. customPurification
  3. dissolutionHPLC (pH=11, small column, sample dissolved in methanol/water (50/50), gradient 0-40, 20 minutes)

Sources & evidence

ORD record
ord-78f47f8c250849c6b903e265dab16afa
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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