Hydrochloric Acid → 3-(4-Bromophenyl)oxetan-3-amine hydrochloride

HRID 1047040ノート

反応式

HRID 1047040 の反応式
[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]=1

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 67067894N-(3-(4-bromophenyl)oxetan-3-yl)-2-methylpropane-2-sulfinamide

生成物 1

HCID 566046653-(4-Bromophenyl)oxetan-3-amine hydrochloride

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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].

後処理

  1. filtrationFiltration

出典と根拠

ORDレコード
ord-c558befcc38146e59da07d27963acaf3
出典データセット
uspto-grants-2013_10
特許番号
US08569331B2

反応ノート

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