Allyl chloroformate → HCID 15117212, compound
Reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:11](=[O:13])[CH3:12])([OH:10])[CH2:6][CH2:5]1)(=[O:3])C.ClC([O:17][CH2:18][CH:19]=[CH2:20])=O.[H-].[K+]>Cl.O1CCCC1.O.C(OCC)(=O)C>[C:11]([C:7]1([OH:10])[CH2:8][CH2:9][N:4]([C:1]([O:17][CH2:18][CH:19]=[CH2:20])=[O:3])[CH2:5][CH2:6]1)(=[O:13])[CH3:12]Participants
Conditions
- Temperature
- 100 °C
Procedure
1,4-Diacetyl-4-hydroxypiperidine (0.2 g) was dissolved in 1N hydrochloric acid (4 ml) and the solution was heated at 100° C. for 15 hours. After cooling to 0° C., the reaction mixture was diluted with a mixture of tetrahydrofuran (10 ml) and water (10 ml). To the mixture was added dropwise at 0° C. a solution of allyl chloroformate (0.15 ml) in tetrahydrofuran (2 ml) while adjusting pH to around 10 with aqueous potassium hydride. After stirring at 0° C. for 30 minutes, the reaction mixture was diluted with a mixture of ethyl acetate and water. The organic layer was separated, washed in turn with water and brine, and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (10 g) eluting with a mixture of n-hexane and ethyl acetate (9:1-1:1, V/V) to give 4-acetyl-1-allyloxycarbonyl-4-hydroxypiperidine (0.26 g).
Workup
- temperatureAfter cooling to 0° C.
- customThe organic layer was separated
- washwashed in turn with water and brine
- dry with materialdried over magnesium sulfate
- customEvaporation of the solvent
- customgave a residue, which
- customwas chromatographed on silica gel (10 g)
- washeluting with a mixture of n-hexane and ethyl acetate (9:1-1:1, V/V)
Sources & evidence
- ORD record
- ord-9301b43019d2412c8ea849b8d6817473
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05102877
Reaction notes
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