Hydrochloric Acid → 3-(4-Bromophenyl)oxetan-3-amine hydrochloride
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:12]S(C(C)(C)C)=O)[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.[ClH:19]>ClCCl.C(OCC)(=O)C.CCCCCC>[ClH:19].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH2:12])[CH2:9][O:10][CH2:11]2)=[CH:6][CH:7]=1Participants
Procedure
To a solution of N-[3-(4-bromophenyl)oxetan-3-yl]-2-methylpropane-2-sulfinamide (284 mg) in dichloromethane (17 mL) was added a solution of hydrogen chloride in ethyl acetate (4 M, 427 μl) dropwise at room temperature. After being stirred at the same temperature for 30 min, the reaction mixture was diluted with hexane. Filtration gave 3-(4-bromophenyl)oxetan-3-amine hydrochloride. To a solution of 3-(4-bromophenyl)oxetan-3-amine hydrochloride in THF (10 mL) and saturated sodium bicarbonate aqueous solution (10 mL) was added a solution of di-tert-butyl dicarbonate (403 mg) in THF (10 mL) dropwise. After being stirred at room temperature for 48 h, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate aqueous solution then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (5-30% ethyl acetate in hexanes) gave the product (194 mg, 2 steps 69%). 1HNMR (CDCl3) 400 MHz δ: 7.53 (d, J=8.7 Hz, 2H), 7.42 (d, J=8.7 Hz, 2H), 5.29 (br s, 1H), 5.01-4.90 (m, 2H), 4.85-4.73 (m, 2H), 1.50-1.26 (m, 9H). LCMS: 328, 330 [M+H].
Workup
- filtrationFiltration
Sources & evidence
- ORD record
- ord-c558befcc38146e59da07d27963acaf3
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569331B2
Reaction notes
Loading…