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934664-41-2

Basic Information
CAS No.: 934664-41-2
Name: 1-Boc-3-methylideneazetid...
Article Data: 20
Molecular Structure:
Molecular Structure of 934664-41-2 (1-Boc-3-methylideneazetid...)
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
Synthetic route
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

1779-49-3

Methyltriphenylphosphonium bromide

934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
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%
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium tert-butylate; methyl-triphenylphosphonium iodide In diethyl ether at 35℃; for 2h;99%
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

2065-66-9

methyl-triphenylphosphonium iodide

934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
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%
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

triphenylphosphine methyl bromide

934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium tert-butylate In diethyl ether at 20℃;61%
24424-99-5

di-tert-butyl dicarbonate

934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
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
141699-55-0

tert-butyl 3-hydroxyazetidine-1-carboxylate

934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
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
934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

5,5-dimethyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester

C17H28N2O5

Conditions
ConditionsYield
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%
934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

81290-20-2

(trifluoromethyl)trimethylsilane

tert-butyl 1,1-difluoro-5-azaspiro[2.3]hexane-5-carboxylate

Conditions
ConditionsYield
With sodium iodide In tetrahydrofuran for 8h; Reflux;91%
With sodium iodide In tetrahydrofuran at 65℃; Inert atmosphere;64%
934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

142253-56-3

3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
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%
934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

C14H17NO4

C23H32N2O6

Conditions
ConditionsYield
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%
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    934664-41-2

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