Methyl iodide → (+/-)-Methyl N,N'-dibenzyloxycarbonylpiperazine-2-carboxylate

HRID 582227노트

반응식

HRID 582227 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH:12]1[C:27]([OH:29])=[O:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:32](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:13][CH:12]1[C:27]([O:29][CH3:32])=[O:28])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 226328591,4-Bis(benzyloxycarbonyl)piperazine-2-carboxylic acid

생성물 1

HCID 21847669(+/-)-Methyl N,N'-dibenzyloxycarbonylpiperazine-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a flask containing N,N'-dibenzyloxycarbonylpiperazine-2-carboxylic acid (Step 1, 12.83 g, 32.20 mmol) dissolved in dry DMF (50 mL) is added methyl iodide (5.6 mL, 90.00 mmol) and potassium carbonate (4.60 g, 32.20 mmol). The mixture is stirred for 4 hours at ambient temperature under an inert atmosphere. The reaction is concentrated in vacuo, diluted with ethyl acetate (150 mL), washed with water (3×50 mL) and saline, dried over MgSO4, concentrated in vacuo, and chromatographed on silica gel (70-230 mesh), eluting with hexane/ethyl acetate (50/50). The appropriate fractions are combined (Rf =0.55, TLC, hexane/ethyl acetate, 50/50) and concentrated in vacuo to give the title compound, NMR (CDCl3) 7.31, 5.15, 5.12, 4.70, 4.1-2.9.

후처리

  1. concentrationThe reaction is concentrated in vacuo
  2. additiondiluted with ethyl acetate (150 mL)
  3. washwashed with water (3×50 mL) and saline
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (70-230 mesh)
  7. washeluting with hexane/ethyl acetate (50/50)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a626d09972e949b49600f0b7114a58f7
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922707

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