N-bromobutanimide → Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)piperidine-1-carboxylate

HRID 1518536노트

반응식

HRID 1518536 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C1C(=O)N([Br:26])C(=O)C1>C(#N)C>[Br:26][C:5]1[S:1][C:2]([CH:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)=[N:3][CH:4]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 58179889Tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate

생성물 1

HCID 58180056Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate (530 mg, 1.97 mmol) in acetonitrile (10 mL) was added NBS (1.40 g, 7.86 mmol). The mixture was stirred at RT for 14 hours and heated at 50° C. for 4 hours. The reaction mixture with some starting material recovered was poured into a solution of Na2SO3 (30 mL) and 6N NaOH (2 mL). The aqueous layer was extracted with EtOAc, dried over MgSO4, and the combined organics concentrated in vacuo. The residue was purified by silica gel chromatography to provide tert-butyl 4-(5-bromothiazol-2-yl)piperidine-1-carboxylate as a yellow oil [210 mg (0.61 mmol); 1H NMR (300 MHz, CDCl3) 7.59 (s, 1H), 4.20 (brd, J=12.9 Hz, 2H), 3.13 (tt, J=3.8, 11.5 Hz, 1H), 2.89 (t, J=11.6 Hz, 2H), 2.08 (d, J=11.7 Hz, 2H), 1.72 (dq, J=4.3, 11.9 Hz, 2H), 1.49 (s, 9H)].

후처리

  1. temperatureheated at 50° C. for 4 hours
  2. customThe reaction mixture with some starting material recovered
  3. additionwas poured into a solution of Na2SO3 (30 mL) and 6N NaOH (2 mL)
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. concentrationthe combined organics concentrated in vacuo
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-d80e8f75fc584087a7d8dd5cf4260653
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232406B2

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