1-Boc-3-iodoazetidine

Colorless to red-brown liquid

STAP B tert-butyl 3-iodoazetidine- 1 -carboxylate. [Chem.10][0206] To a solution of tert-butyl 3-hydroxyazetidine-l-carboxylate (3.35 g, 19.3 mmol) in toluene (200 mL) was added imidazole (3.95 g, 58.0 mmol), triphenylphosphine (10.1 g, 38.7 mmol) and iodine (7.36 g, 29.0 mmol). The mixture was heated for 100A solution of 3-hydroxy-azetidine-i-carboxylic acid tert-butyl ester (3.35 g, 19.34 mmol) in toluene (200 ml) was treated with imidazole (3.95 g, 58.01 mmol), triphenyl- phosphine (10.14 g, 38.65 mmol) and IA solution of 3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (3.35 g, 19.34 mmol) in toluene (200 ml) was treated with imidazole (3.95 g, 58.01 mmol), triphenyl- phosphine (10.14 g, 38.65 mmol) and I2 (7.36 g, 28.99 mmol). The mixture was heated at 100A solution of ieri-butyl 3-hydroxyazetidine-l-carboxylate (25-3) (3.5 g, 0.02 mol) in toluene (200 mL) was treated with imidazole (4.08 g, 0.06 mol), PPhExample 206a To a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (400 mg, 2.31 mmol) in toluene (23 ml), imidizole (472 mg, 6.93 mmol), triphenylphosphine (1.21 g, 4.62 mmol) and iodine (879 mg, 3.46 mmol) were added successively and the reaction mixture was heated at 110° C. for 4 h. (1) To a solution of Compound 1 (2.0 g) in toluene (115 mL) was added imidazole (2.36 g), triphenylphosphine (6.06 g), and iodine (4.4 g), and the mixture was stirred at 100°C for 1 hour and 45 minutes. The reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, stirred, then iodine was added thereto, stirred, and extracted with ethyl acetate. The resultant organic layer was dried, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=100:0-75:25) to give Compound 2 (3.23 g) as a colorless liquid.Potassium iodide (12.9 g, 77.7 mmol) and C6 (6.5 g, 26.0 mmol) were combined in DMF (40 mL). Tert-butyl 3-((methylsulfonyl)oxy)azetidin-1-carboxylate (2.67 g, 10.62 mmol) was dissolved in 20mL N, N-dimethyl formamide, and potassium iodide (5.3 g, 31.93 mmol) was added. Preparation 58 tert-Butyl 3-iodoazetidine-i-carboxylate; tert-Butyl 3-(methylsulfonyloxy)azetidine-1-carboxylate (Preparation 57, 8Og, 0.318 mol) and potassium iodide (159g, 0.96 mol) were mixed in dimethylformamide (500 ml_). The reaction mixture was stirred at 11OProduction Example 26-3 Preparation 32 To a flame-dried 500 mL round bottom flask was added 1-amino-2, 3-dibromopropane hydrobromide (17) (7.5 g, 0.025 mol, 1 equiv.) and stirred without solvent to obtain 17 asa fine powder under argon (alternatively, crystals of 17 could be ground to a fine powder by hand before use).Dry THF (75 mL) was added to the flask and cooled to –78 oC. PhLi solution (1.8M in dibutyl ether, 39.8 mL, 0.075 mol, 3 equiv.) was slowly added via syringe and the reaction mixture stirred at –78 oC for 2 h. To theresulting mixture was added MeCN (240 mL), NaI (11.4 g, 0.075 mol, 3 equiv.) and Boc2O (11.2 mL, 0.050 mol, 2 equiv.) at –78 oC and warmed at rt overnight. The resulting mixture was poured into water (200 mL), washedwith sat. aq. Na2S2O3 (100 mL) and then extracted with ethyl acetate (3 x 150 mL). The combined organiclayers were washed with brine (100 mL), dried over Na2SO4, and concentrated. The crude material waspurified by flash chromatography (silica gel, 5–40percent EtOAc in hexanes) to give the desired product 6 (5.8 g, 81percent). Physical State: light yellow oil; Rf = 0.55 (2:8 EtOAc/hexanes, vis. UV); 1H NMR (500 MHz, CDCl3): δ 4.67 –4.60 (m, 2H), 4.50 – 4.43 (m, 1H), 4.33 – 4.24 (m, 2H), 1.44 (s, 9H); 13C NMR (126 MHz, CDCl3): δ 155.7, 80.3, 61.7 (br, 2C), 28.4 (3C), 2.7; HRMS (ESI-TOF): calc’d for C8H14INNaO2 [M+Na+] 305.9967; found 305.9950.Radical iodo-de-caboxylation induced by TV-iodo amides/V-iodo amideR-COOH *- R-lGeneral procedure[00111] Procedure: A mixture of R-COOH (1 mmol), N-iodo amide (1-4 equiv), and solvent (3-6 mL) was refluxed (Δ) for 1-24 h in the dark (NL) or under irradiation with 500 W tungsten lamp (TL) or under fluorescent room lighting (FL).[00112] Treatment: The reaction mixture was cooled to rt, and washed with aq NaHS0

Molecular Weight:283.11
XLogP3:1.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:283.00693
Monoisotopic Mass:283.00693
Topological Polar Surface Area:29.5
Heavy Atom Count:12
Complexity:182
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes