3-Hydroxypiperidine → 1-[2-Hydroxy-2-(5-phenyl-1,2-oxazol-3-yl)ethyl]piperidin-3-ol
Reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][N:5]=1.[OH:15][CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1>>[OH:1][CH:2]([C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][N:5]=1)[CH2:3][N:18]1[CH2:19][CH2:20][CH2:21][CH:16]([OH:15])[CH2:17]1Participants
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 3-(1,2-epoxyethyl)-5-phenylisoxazole (1.05 g) and 3-hydroxypiperidine (1.13 g) is heated at 70°C for 20 minutes and then chromatographed on silica gel to give 3-[1-hydroxy-2-(3-hydroxypiperidino)ethyl]-5-phenylisoxazole (1.25 g). To a suspension of the compound in water (6.5 ml) is added 60% perchloric acid (516 ml), the precipitate is collected by filtration, and recrystallized from a mixture of 99% ethanol (2 ml) and ethyl acetate (8 ml) to give the perchlorate which melts at 151°-153°C. The perchlorate is suspended in aqueous sodium hydroxide solution and extracted with methylene chloride. After being dried with sodium sulfate, the extract is evaporated to give 3-[1-hydroxy-2-(3-hydroxypiperidino) ethyl]-5-phenylisoxazole (544 mg). Recrystallization from a mixture of ethyl acetate and hexane gives colorless prisms (388 mg) melting at 94°-96°C.
Workup
- customchromatographed on silica gel
Sources & evidence
- ORD record
- ord-b5bde49b583f41d891a496082efd9a42
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03932426
Reaction notes
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