Hydrogen Bromide → Ethyl 3-bromo-4-oxopiperidine-1-carboxylate

HRID 1529542노트

반응식

HRID 1529542 반응식
[Br:1]Br.[C:3]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)([O:5][CH2:6][CH3:7])=[O:4].Br>O.C1COCC1>[CH2:6]([O:5][C:3]([N:8]1[CH2:9][CH2:10][C:11](=[O:14])[CH:12]([Br:1])[CH2:13]1)=[O:4])[CH3:7]

참가 물질

6

반응물 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

생성물 1

HCID 13799628Ethyl 3-bromo-4-oxopiperidine-1-carboxylate수율 108%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Bromine (2.83 mL, 55 mmol) was added dropwise to a stirred solution of N-carbethoxy-4-piperidone (7.54 mL, 50 mmol) and a 48% solution of HBr in H2O (1.41 mL) in THF (88 mL) at 0° C. The mixture was stirred at room temperature for 15 minutes and then quenched with a saturated solution of Na2S2O3, basified with a saturated solution of Na2CO3 and extracted with diethyl ether. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 3-bromo-4-oxo-1-piperidinecarboxylic acid ethyl ester (13.5 g, 54% yield, 50% pure) as a dark brown oil that was used in the next step without further purification. C8H12BrNO3 GCMS (EI): Rt 3.77, MW (theor) 249; m/z [M]+ 249 (using method, GC-MS Method 2).

후처리

  1. customat 0° C
  2. customquenched with a saturated solution of Na2S2O3
  3. extractionextracted with diethyl ether
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo

출처 및 근거

ORD 기록
ord-146ab7320c0c43b1b23bae314d6c6779
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090632B2

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