Methyl iodide → 4-Cbz-1-methyl-2-piperazinone

HRID 646932

반응식

HRID 646932 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]C([O-])(C)C.[K+].CI>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:18])[C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 586385404-Cbz-1-methyl-2-piperazinone수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-oxo-piperazine-1-carboxylic acid benzyl ester (2.00 g, 8.54 mmol) in DMF (30 mL) was added KOtBu (1.54 g, 13.7 mmol) under Ar. The resulting solution was stirred at room temperature for 15 min and cooled to 0° C. MeI (0.85 mL, 14 mmol) was then added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. DMF was removed in vacuo and the residue was chromatographed on silica (5-50% EtOAc:hexane) to obtain the title compound (1.40 g, 66%). 1H-NMR (CDCl3; 400 MHz): δ 7.32 (m, 5H), 5.13 (s, 2H), 4.13 (s, 2H), 3.70 (m, 2H), 3.34 (m, 2H), 2.97 (s, 3H)

후처리

  1. temperaturecooled to 0° C
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 h
  4. customDMF was removed in vacuo
  5. customthe residue was chromatographed on silica (5-50% EtOAc:hexane)

출처 및 근거

ORD 기록
ord-ebc6365f48494669a8f43f49246418fa
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705042B2

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