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With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 5 - 20℃; for 6 h;
A 30percent aqueous solution of NaOH (1.99 mL; 19.9 mmol) was added gradually to a solution of p-toluenesulfonyl chloride (2.6 g; 13.6 mmol) and benzyltriethylammonium chloride (CAS 56-37-1 ) (0.194 g; 0.85 mmol) in toluene (5 mL) at 5°C. 3- Oxetanemethanol (CAS 6246-06-6) (0.915 mL; 11.35 mmol) was added drop wise below 10°C. The reaction mixture was stirred below 10°C for 1 hour and at room temperature for 5 hours. The reaction mixture was poured into ice and extracted with DCM (3 times). The organic layer was dried over MgS04, filtered and the solvent was evaporated to give 2.49 g (91 percent) of intermediate 49.
70%
With dmap; triethylamine In dichloromethane at 20℃; for 3 h;
To a solution of oxetan-3-ylmethanol (750 mg, 8.5 mmol) in DCM (15ml) was added N,N-dimethylpyridin-4-amine (122 mg, 1 mmol), TEA (2.0 g, 20 mmol) and4-methylbenzenesulfonyl chloride (1.6 g, 8.5 mmol). The mixture was stirred at rt for 3 h,concentrated, and the residue was purified by column chromatography using ethyl acatatein petroleum ether (1/4) to afford oxetan-3-ylmethyl4-methylbenzenesulfonate (1.4 g, 70percentyield). LCMS (ESI) m/z: 243.3 (M + 1t.
45%
Stage #1: With dmap; triethylamine In dichloromethane at 0℃; for 0.0833333 h; Inert atmosphere Stage #2: at 0℃; for 6 h; Inert atmosphere
[00551] A mixture of 166-1 (200.00 mg, 2.27 mmol, 1.00 eq), TEA (459.38 mg, 4.54 mmol, 629.29 uL, 2.00 eq) and DMAP (27.73 mg, 227.00 umol, 0.10 eq) in DCM (10.00 mL) was stirred at 0C for 5 min under N2. Then 4-methylbenzenesulfonyl chloride (454.39 mg, 2.38 mmol, 1.05 eq) was added, and the mixture was stirred at 0C for 1 h. The crude LCMS showed no desired product MS value was detected, and the mixture was stirred at 0C for an additional 5 h. TLC(PE:EtOAc=2: l UV) indicated 166-1 was consumed completely and one new spot formed. The reaction mixture was diluted with DCM (20 mL), washed with brine (20 mL), and then extracted with DCM (25 mL*3). The combined organic layers were dried over Na2S04, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography to give 166-2 (0.25 g, 1.02 mmol, 45.00percent yield).
1 g
With dmap; triethylamine In dichloromethane at 15℃; for 16 h;
Step 1: Preparation of oxetan-3-ylmethyl 4-methylbenzenesulfonate To a stirred solution of 3-oxetanemethanol (500 mg, 5.67 mmol) in DCM (5 mL) was added Et3N (1.0 g, 10.2 mmol) and DMAP (70 mg, 0.57 mmol). Then to the mixture was added a solution of 4-methylbenzenesulfonyl chloride (1.6 g, 8.51 mmol) in DCM (5 mL) dropwise. After being stirred at 15 oC for 16 hrs, the resulting mixture was diluted with DCM (50 mL), washed with H2O (20 mL), 2 N HCl (20 mL) and brine (10 mL), then dried over anhydrous Na2SO4 and concentrated in vacuo to give oxetan-3-ylmethyl 4-methylbenzenesulfonate (1.0 g) as a colorless oil which was used in the next step directly without further purification.
100 mg
With pyridine In dichloromethane at 23 - 29℃; for 16 h;
To a solution of oxetan-3-ylmethanol (CAS registry number 6246-06-6; 100 mg, 1.14 mmol) in DCM (5 mL) were added TsC1 (260 mg, 1.36 mmol) and pyridine (180 mg, 2.27 mmol). Then the reaction was stirred at 23-29 °C for 16 h. TLC (PE: EA = 1: 1) confirmedthat starting material was consumed and a new product was formed. The mixture wasconcentrated and purified by chromatography column on silica gel, eluting with PE: EA = 5:1, to afford oxetan-3-ylmethyl 4-methylbenzenesulfonate (100mg). ‘HNMR (CDC13) 5 7.81(d, J 8.0 Hz, 2H), 7.37 (d, J 8.0 Hz, 2H), 4.73-4.77 (t, J= 6.8 Hz, 2H), 4.32-4.35 (t, J=5.6 Hz, 2H), 4.26 (d, J 7.2 Hz, 2H), 3.26-3.33 (m, 1H), 2.47 (s, 3H).
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