1-Aziridinecarboxylicacid,1,1-dimethylethylester(9CI)

Preparation of t-Boc aziridine Example 47 Example 47 Example 47 Preparation of t-Boc aziridine Synthesis of N2S2 Chelating Agent 9 Synthesis of Diamine 6 Diamine 6 is prepared according to the scheme shown in FIG. 1A and the following description, which refers to compounds by their numbers as set forth in FIG. 1A. To a solution of desoxyanisoin 1 (1.95 mmol) in EtOH (5 mL) is added hydroxylamine hydrochloride (7.20 mmol) followed by pyridine (0.5 mL). The mixture is heated to reflux for 1 hour then cooled and concentrated in vacuo. Water (5 mL) is added. The resulting suspension is stirred for 15 min and then filtered. The filter cake is washed with additional water (2*5 mL) then allowed to air dry. The collected white solid (oxime 2) is of sufficiently high purity to be used in subsequent steps without additional purification. To a stirred suspension of LAH (2.24 mmol) in THF (2 mL) is added, dropwise, a solution of oxime 2 (0.56 mmol) in THF (2 mL). The mixture is allowed to stir under nitrogen at room temperature for 12 hours. The mixture is cooled in ice water and excess LAH is consumed by the careful, dropwise, addition of water. The resulting precipitate is removed by filtration through glass fiber filter paper and washed with ether (3*5 mL). The washings are combined with the original filtrate, dried over sodium sulfate and concentrated in vacuo. The resulting oil is then chromatographed on silica gel (eluding solvent:ethyl acetate/hexane) to give aziridine 3. To a solution of aziridine 3 (1 mmol) in acetonitrile (5 mL) is added di-tert-butyl dicarbonate (1.1 mmol) followed by triethylamine (0.5 mL). The mixture is stirred at room temperature under nitrogen for 16 hours then concentrated in vacuo. The resulting oil is dissolved in ethyl acetate and washed with 1N aqueous HCl and brine. Drying over magnesium sulfate and concentration yields the Example 47 N-Boc aziridine 166: Boc anhydride (113 mg, 0.52 mmol) was added to a solution of aziridine 165 (125 mg, 0.49 mmol), triethylamine (70 muL), DMAP (cat. amount) in dichloromethane (7 mL). After 1 h the reaction was concentrated and the residue subjected to flash chromatography (40percent EtOAc in hexanes) to give 154 mg (88percent) of the N Boc aziridine 166 as a pale oil. 1 H NMR (CDCl3, 300 MHz): delta 6.82 (m, 1H); 4.47 (br m, 1H); 4.23 (t, 2H, J=4.7 Hz); 3.81 (t, 2H, J=4.7 Hz); 3.75 (s, 3H); 3.00 (br d, 1H, J=18.0 Hz); 2.90-2.85 (m, 2H); 2.65-2.55 (m, 1H); 2.10 (s, 3H); 1.44 (s, 9H).Example 47 N-Boc aziridine 166: Boc anhydride (113 mg, 0.52 mmol) was added to a solution of aziridine 165 (125 mg, 0.49 mmol), triethylamine (70 muL), DMAP (cat. amount) in dichloromethane (7 mL). After 1 h the reaction was concentrated and the residue subjected to flash chromatography (40percent EtOAc in hexanes) to give 154 mg (88percent) of the N Boc aziridine 166 as a pale oil. 1 H NMR (CDCl3, 300 MHz): delta6.82 (m, 1H); 4.47 (br m, 1H); 4.23 (t, 2H, J=4.7 Hz); 3.81 (t, 2H, J=4.7 Hz); 3.75 (s, 3H); 3.00 (br d, 1H, J=18.0 Hz); 2.90-2.85 (m, 2H); 2.65-2.55 (m, 1H); 2.10 (s, 3H); 1.44 (s, 9H).Example 47 N-Boc aziridine 166: Boc anhydride (113 mg, 0.52 mmol) was added to a solution of aziridine 165 (125 mg, 0.49 mmol), triethylamine (70 muL), DMAP (cat. amount) in dichloromethane (7 mL). After 1 h the reaction was concentrated and the residue subjected to flash chromatography (40percent EtoAc in hexanes) to give 154 mg (88percent) of the N Boc aziridine 166 as a pale oil. 1H NMR (CDCl3, 300 MHz): delta 6.82 (m, 1H); 4.47 (br m, 1H); 4.23 (t, 2H, J=4.7 Hz); 3.81 (t, 2H, J=4.7 Hz); 3.75 (s, 3H); 3.00 (br d, 1H, J=18.0 Hz); 2.90-2.85 (m, 2H); 2.65-2.55 (m, 1H); 2.10 (s, 3H); 1.44 (s, 9H).Step 3 To a solution of aziridine (100 g; 2.3 mol) in dioxane (2 L) and water (1 L) the aziridine (100 g; 2.30 mol), cooled to 0° C. in ice water bath, was added di-tert-butyl dicarbonate (530 g; 2.41 mol) in portion over 2 h. The mixture was stirred at r.t. overnight. tert-Butyl aziridine-1-carboxylate LXXXVI was isolated as a mixture with dioxane by distillation.Preparation of

Molecular Weight:143.18
XLogP3:0.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:143.094628657
Monoisotopic Mass:143.094628657
Topological Polar Surface Area:29.3
Heavy Atom Count:10
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes