Triethylamine → N-(p-methoxybenzyloxycarbonyl)-5-fluorotryptamine
Reaction equation
[F:1][C:2]1[CH:13]=[C:12]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:43]=[CH:42][C:26]([CH2:27][O:28][C:29](ON=C(C2C=CC=CC=2)C#N)=[O:30])=[CH:25][CH:24]=1.O1CCOCC1>O>[CH3:21][O:22][C:23]1[CH:43]=[CH:42][C:26]([CH2:27][O:28][C:29]([NH:11][CH2:10][CH2:9][C:8]2[C:12]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:13]=3)[NH:6][CH:7]=2)=[O:30])=[CH:25][CH:24]=1Participants
6
Procedure
To a strirred suspension 1.4 g (7.8 mmol) of 5-fluorotryptamine in 5 mL of water and 1.1 mL (7.8 mmol) of triethylamine was added 2.5 g (7.8 mmol) of 2-(4-methoxybenzyloxycarbonyloxyimino)-2-phenylacetonitrile (MOZ-ON) and 10 mL of dioxane. The reaction mixture was stirred at room temperature for 1 hour under argon, diluted with water, and extracted with ethyl acetate. The organic extracts were washed with saturated sodium chloride, dried over anhydrous Na2SO4, and concentrated under vacuum. The residue was purified by flash chromatography, over silica gel, using hexane:ethyl acetate (2:1 and later 1:1) as eluents to provide 1.7 g (63%) of N-(p-methoxybenzyloxycarbonyl)-5-fluorotryptamine as an off-white solid. mp 118°-119° C.
Workup
- extractionextracted with ethyl acetate
- washThe organic extracts were washed with saturated sodium chloride
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under vacuum
- customThe residue was purified by flash chromatography, over silica gel
Sources & evidence
- ORD record
- ord-33d87a995c4a45d68ccf3f9f191d7c87
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05580878
Reaction notes
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