Triethylamine → 2-(2-Oxazolinyl)pyridine
Reaction equation
[CH2:1]([N:3](CC)CC)[CH3:2].Cl.[NH2:9][C@@H:10]([CH2:13][CH:14]1[CH2:19][CH2:18]CCC1)[CH2:11][OH:12]>C(Cl)Cl>[N:9]1[CH:18]=[CH:19][CH:14]=[CH:13][C:10]=1[C:11]1[O:12][CH2:2][CH2:1][N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Methyl-6-phenylpyridyl-2-imidate (0.160 g, 0.754 mmol) was dissolved in CH2Cl2 (3 mL). Triethylamine (0.12 mL, 0.83 mmol) was added followed by 2-(S)-amino-3-cyclohexylpropanol hydrochloride (0.161 g, 0.829 mmol). The reaction vessel was sealed and heated on a heating block (50° C.) for 16 hours and the resultant solution was then filtered to remove the insoluble salts. The filtrate was loaded onto the top of a Biotage cartridge (silica gel, 40S) and the product was eluted using a stepped gradient of 0 to 30% ethyl acetate in hexanes as the eluent. The product was obtained after evaporation of the eluent as a slightly yellow solid (0.181 g, 75%).
Workup
- customThe reaction vessel was sealed
- filtrationthe resultant solution was then filtered
- customto remove the insoluble salts
- washthe product was eluted
- customThe product was obtained
- customafter evaporation of the eluent as a slightly yellow solid (0.181 g, 75%)
Sources & evidence
- ORD record
- ord-b10be19e57c84d6bb0cfaa769c38af08
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138348B2
Reaction notes
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