Water → 1-(5-Nitropyridin-2-yl)azetidin-3-ol
Reaction equation
Cl.[OH:2][CH:3]1[CH2:6][NH:5][CH2:4]1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1.C(N(CC)CC)C.O>CN(C)C=O.C(OCC)(=O)C>[OH:2][CH:3]1[CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)[CH2:4]1Participants
7
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 0.311 g (2.84 mmol) of 3-hydroxyazetidine hydrochloride, 0.3 g (1.89 mmol) of 2-chloro-5-nitropyridine and 0.41 mL (2.84 mmol) of triethylamine in 10 mL of dimethylformamide is heated overnight at 100° C. After this time, the suspension is poured into a mixture of 30 mL of water and 30 mL of ethyl acetate. The aqueous phase is separated, and then extracted with 20 mL of ethyl acetate. The organic phases are combined, washed three times with 25 mL of water, then dried over sodium sulfate and concentrated at reduced pressure. We thus obtain 0.34 g of the expected product in the form of a solid, which will be used as it is in the rest of the synthesis.
Workup
- customThe aqueous phase is separated
- extractionextracted with 20 mL of ethyl acetate
- washwashed three times with 25 mL of water
- dry with materialdried over sodium sulfate
- concentrationconcentrated at reduced pressure
- customis in the rest of the synthesis
Sources & evidence
- ORD record
- ord-768490844d0f4021b652026ce9cf0667
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716273B2
Reaction notes
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