Water → Benzyl 4-bromopiperidine-1-carboxylate

HRID 1269768

반응식

HRID 1269768 반응식
Br.[Br:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH2:9]([O:16][C:17](ON1C(=O)CCC1=O)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN1CCOCC1.O>O1CCCC1>[Br:2][CH:3]1[CH2:8][CH2:7][N:6]([C:17]([O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])[CH2:5][CH2:4]1

참가 물질

6

반응물 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 83172Benzyl succinimido carbonateHCID 27346764-Bromopiperidine Hydrobromide

생성물 1

HCID 2776275Benzyl 4-bromopiperidine-1-carboxylate수율 98.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-bromopiperidine hydrobromide (3.0 g, 12.2 mmol) in tetrahydrofuran (30 ml) were added 1-{[(benzyloxy)carbonyl]oxy}-2,5-pyrrolidinedione (3.20 g, 12.9 mmol), N-methylmorpholine (1.62 ml, 14.7 mmol) and 4-N,N-dimethylaminopyridine (30 mg) at room temperature, and stirred at room temperature for 16 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a 1N-aqueous hydrochloric acid solution, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to obtain benzyl 4-bromo-1-piperidinecarboxylate (3.58 g, 98%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a 1N-aqueous hydrochloric acid solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-8ffc2216144248a1b5320f2e36839be0
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199147B2

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