HCID 131730371, compound → HCID 46938040, compound

HRID 1963348Notes

Reaction equation

HRID 1963348 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 131730371HCID 131730371, compound

Product 1

HCID 46938040HCID 46938040, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Racemic trans-methyl 2-isobutyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.39 g, 1.3 mmol) was stirred in HBr (33% in HOAc) 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 0-25% acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 10 minutes with a flow of 100 mL/minutes. The title compound (0.26 g) was isolated. 1H NMR (600 MHz, d2o) δ 0.76 (d, 3H), 0.79 (d, 3H), 1.14 (m, 1H), 1.33-1.41 (m, 1H), 1.45 (m, 1H), 1.59 (m, 1H), 1.76 (m, 1H), 1.98 (m, 1H), 2.06 (m, 1H), 2.21 (m, 1H), 3.04 (m, 2H), 3.14-3.31 (m, 4H), 5.67 (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-ae6d8c17eff84d6fa9456ede4f7ff464
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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