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

HRID 646932

反応式

HRID 646932 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 586385404-Cbz-1-methyl-2-piperazinone収率 66%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-ebc6365f48494669a8f43f49246418fa
出典データセット
uspto-grants-2010_04
特許番号
US07705042B2

関連ノート

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