| Identification | Back Directory | [Name]
3-Ethynyl-1-azetidinecarboxylic acid tert-butyl ester | [CAS]
287193-01-5 | [Synonyms]
1-Boc-3-ethynylazetidine
1-Boc-3-methylazetidine,95%
tert-butyl 3-ethynylazetidine-1-carboxylate
3-Ethynyl-1-azetidinecarboxylic acid tert-butyl ester
1-Azetidinecarboxylic acid, 3-ethynyl-, 1,1-dimethylethyl ester | [Molecular Formula]
C10H15NO2 | [MDL Number]
MFCD17016080 | [MOL File]
287193-01-5.mol | [Molecular Weight]
181 |
| Chemical Properties | Back Directory | [Boiling point ]
228℃ | [density ]
1.05 | [Fp ]
92℃ | [storage temp. ]
2-8°C | [pka]
-2.81±0.40(Predicted) | [Appearance]
Colorless to off-white Liquid | [InChI]
InChI=1S/C10H15NO2/c1-5-8-6-11(7-8)9(12)13-10(2,3)4/h1,8H,6-7H2,2-4H3 | [InChIKey]
UENGYBYGCXKNRF-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CC(C#C)C1 |
| Hazard Information | Back Directory | [Synthesis]
To a stirred solution of tert-butyl 3-formylazetidine-1-carboxylate (1.3 g, 27 mmol) in methanol (70 ml) was added dimethyl (1-diazido-2-oxopropyl)phosphonate (6 g, 31.2 mmol) followed by potassium carbonate (14.92 g, 108 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 3 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (150 ml), filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by fast chromatography (silica gel, eluent: 0-100% hexane solution of ethyl acetate) to give tert-butyl 3-alkynyl-1-azetidinecarboxylate (4.6 g, 94%).1H NMR (400 MHz, DMSO-d6) δ 1.34 (s, 9H), 3.22-3.23 (m, 1H), 3.34-3.39 (m, 1H ), 3.68 (t, J = 6.8 Hz, 2H), 4.04 (t, J = 8.4 Hz, 2H). | [References]
[1] Patent: WO2014/165075, 2014, A1. Location in patent: Page/Page column 46; 47
[2] Patent: WO2016/4413, 2016, A2. Location in patent: Paragraph 0279
[3] Patent: US2018/86709, 2018, A1. Location in patent: Paragraph 0358-0359
[4] Patent: WO2015/51244, 2015, A1. Location in patent: Paragraph 00655; 00709
[5] Patent: WO2016/105485, 2016, A2. Location in patent: Paragraph 0219 |
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