Borane;tetrahydrofuran → 4-Aminomethyl-1-(1-naphthylsulfonyl)piperidine

HRID 2110832노트

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HRID 2110832 반응식
[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5]1)=O.B.O1CCCC1>O1CCCC1>[NH2:1][CH2:2][CH:4]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5]1

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 239932921-(Naphthylsulfonyl)piperidine-4-carboxamide

생성물 1

HCID 688620304-Aminomethyl-1-(1-naphthylsulfonyl)piperidine수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To a solution of 4-aminocarbonyl-1-(1-naphthylsulfonyl)piperidine (10.6 g, 33.3 mmol) in tetrahydrofuran (200 mL) stirring under argon at room temperature, was added borane-tetrahydrofuran complex (1.5 M in tetrahydrofuran, 67 mL, 100 mmol). The resulting solution was heated to 80° C. for 6 h before the solvent was evaporated under vacuum. The residue was dissolved in 1.0 M aqueous hydrochloric acid (100 mL), and this was washed with diethyl ether (100 mL twice). The aqueous layer was basified to pH 10 with 50% aqueous sodium hydroxide and extracted with dichloromethane (50 mL three times). The combined dichloromethane extracts were dried (anhydrous sodium sulfate) and evaporated under vacuum to obtain 4-aminomethyl-1-(1-naphthylsulfonyl)piperidine (9.1 g, 90% yield).

후처리

  1. customwas evaporated under vacuum
  2. dissolutionThe residue was dissolved in 1.0 M aqueous hydrochloric acid (100 mL)
  3. washthis was washed with diethyl ether (100 mL twice)
  4. extractionextracted with dichloromethane (50 mL three times)
  5. dry with materialThe combined dichloromethane extracts were dried (anhydrous sodium sulfate)
  6. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-96211a1ab580490d902bc8dbc4f521a4
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517991B2

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