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CAS No. : | 158602-36-9 | MDL No. : | MFCD17015919 |
Formula : | C10H18INO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OGFCVYKPYPPCDL-UHFFFAOYSA-N |
M.W : | 311.16 | Pubchem ID : | 19034125 |
Synonyms : |
|
Chemical Name : | tert-Butyl 3-(2-iodoethyl)azetidine-1-carboxylate |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; triphenylphosphine; | STR58 N-BOC-Azetidin-3-ylethyl iodide (134) A stirred solution of 133 (0.78 g, 3.8 mmol), PPh3 (1.1 g, 4.3 mmol), imidazole (0.40 g, 5.8 mmol), and CH3 CN (20 mL) at 0 C. was treated with iodine (1.0 g, 4.3 mmol). After 15 min the cooling bath was removed and stirring continued for 5 h. The reaction mixture was then diluted with H2 O and extracted with hexanes (5*25 mL then 4*50 mL). The combined extracts were dried (MgSO4) and concentrated. Flash chromatography (silica, 20% EtOAc/hexanes) gave 134 (0.99 g) as a colorless oil. Rf 0.44 (silica, 20% EtOAc/hexanes). 1 H NMR (400 MHz, CDCl3) delta 4.04 (t, J=7 Hz, 2H), 3.57 (dd, 2H), 3.10 (t, 2H), 2.64 (m, 1H), 2.16 (q, 2H), 1.43 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisopropylamine; In tetrahydrofuran; | STR59 3-[N-BOC-2-(Azetidin-3-yl)ethyl]-2-piperidone (136) A solution of 135 (for preparation see; D. H. Hua, et. al., JOC, 55, 3682, 1990) (0.19 g, 1.2 mmol) in THF (3.9 mL) at -78 C. was added LDA (0.58 mL, 1.2 mmol, 2.0M/heptane/THF/ethylbenzene) dropwise. After 15 min 134 (0.30 g, 0.96 mmol) in THF (3.5 mL) was added dropwise. After stirring 1.0 h, the reaction was quenched with CH3 OH (7.5 mL) and the resulting solution warmed to ambient temperature. The solution was then diluted with EtOAc and then washed with H2 O, 5% KHSO4, sat. NaHCO3, and brine, dried (MgSO4), and concentrated to give 136 (0.27 g) as a white solid. Rf 0.25 (silica, 2:1 CH2 Cl2 /acetone). 1 H ITMR (400 MHz, CDCl3) delta 5.81 (bs, 1H), 3.95 (m, 2H), 3.54 (m, 2H), 3.10 (m, 2H), 2.47 (m, 1H), 2.26 (m, 1H), 2.00-1.40 (m, 8H), 1.43 (s, 9H). |