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CAS No.: | 934664-41-2 |
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Name: | 1-Boc-3-methylideneazetid... |
Article Data: | 20 |
Molecular Structure: | |
Formula: | C9H15NO2 |
Molecular Weight: | 169.224 |
Synonyms: | tert-butyl 3-methylideneazetidine-1-carboxylate |
Density: | 1.02±0.1 g/cm3(Predicted) |
Boiling Point: | 214.8±29.0 °C(Predicted) |
PSA: | 29.54000 |
LogP: | 1.73120 |
tert-butyl 3-oxoazetidine-1-carboxylate
Methyltriphenylphosphonium bromide
3-methylene-azetidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
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Stage #1: potassium tert-butylate; Methyltriphenylphosphonium bromide In diethyl ether at 20℃; for 1h; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In diethyl ether at 35℃; for 2h; | 100% |
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 1h; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In diethyl ether at 35℃; for 2h; | 100% |
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 1h; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In diethyl ether at 35℃; for 2h; | 100% |
tert-butyl 3-oxoazetidine-1-carboxylate
3-methylene-azetidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
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With potassium tert-butylate; methyl-triphenylphosphonium iodide In diethyl ether at 35℃; for 2h; | 99% |
tert-butyl 3-oxoazetidine-1-carboxylate
methyl-triphenylphosphonium iodide
3-methylene-azetidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
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Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at 10 - 20℃; for 2h; | 96% |
tert-butyl 3-oxoazetidine-1-carboxylate
3-methylene-azetidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
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With potassium tert-butylate In diethyl ether at 20℃; | 61% |
di-tert-butyl dicarbonate
3-methylene-azetidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: triethylamine / methanol / 2.5 h / -10 °C 1.2: -10 °C 2.1: oxalyl dichloride; triethylamine / dichloromethane; dimethyl sulfoxide / 15 h / -78 - 20 °C 3.1: potassium tert-butylate; methyl-triphenylphosphonium iodide / diethyl ether / 2 h / 35 °C View Scheme |
tert-butyl 3-hydroxyazetidine-1-carboxylate
3-methylene-azetidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
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Multi-step reaction with 2 steps 1: oxalyl dichloride; triethylamine / dichloromethane; dimethyl sulfoxide / 15 h / -78 - 20 °C 2: potassium tert-butylate; methyl-triphenylphosphonium iodide / diethyl ether / 2 h / 35 °C View Scheme |
3-methylene-azetidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
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With fac-tris(2-(4,6-difluorophenyl)pyridinato,N,C(2'))iridium(III) In acetonitrile at 20℃; Paterno-Buechi Cycloaddition; Irradiation; Sealed tube; Inert atmosphere; regioselective reaction; | 99% |
3-methylene-azetidine-1-carboxylic acid tert-butyl ester
(trifluoromethyl)trimethylsilane
Conditions | Yield |
---|---|
With sodium iodide In tetrahydrofuran for 8h; Reflux; | 91% |
With sodium iodide In tetrahydrofuran at 65℃; Inert atmosphere; | 64% |
3-methylene-azetidine-1-carboxylic acid tert-butyl ester
3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
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Stage #1: 3-methylene-azetidine-1-carboxylic acid tert-butyl ester With borane-THF In tetrahydrofuran at 20℃; for 1h; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 20℃; for 1h; | 90.9% |
Conditions | Yield |
---|---|
With fac-tris(2-(4,6-difluorophenyl)pyridinato,N,C(2'))iridium(III) In acetonitrile at 20℃; Paterno-Buechi Cycloaddition; Irradiation; Sealed tube; Inert atmosphere; regioselective reaction; | 88% |