Methanol → Methyl 2-allyloctanoate
Reaction equation
COC(N([C@@H](C1C=CC=CC=1)C)C(=O)[CH:7]([CH2:14][CH:15]=[CH2:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=O.[CH3:26][O-:27].[Na+].[CH3:29][OH:30]>>[CH2:11]([CH:10]([CH2:9][CH2:8][CH2:7][CH2:14][CH2:15][CH3:16])[C:26]([O:30][CH3:29])=[O:27])[CH:12]=[CH2:13]Participants
4
Procedure
A solution of 0.345 g (1.0 mmol) of N-methyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine in 5 ml of methanol was cooled to 0° C., 0.386 g (2.0 mmol) of NaOMe (28% solution in methanol) was added, and the mixture was stirred for 22 hours. The reaction was terminated by addition of 2 ml of 1 N hydrochloric acid, and the product was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was isolated/purified on a silica gel column to give 0.10 g (51%) of the title compound. N-(2-Allyloctanoyl)-(R)-1-phenylethylamine was formed as a byproduct in 45% yield.
Workup
- customThe reaction was terminated by addition of 2 ml of 1 N hydrochloric acid
- extractionthe product was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous sodium sulfate
- distillationthe solvent was distilled off
- customthe residue was isolated/purified on a silica gel column
Sources & evidence
- ORD record
- ord-ccda876f51db4a96885311fbfdbb1489
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282605B2
Reaction notes
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