Dimethylformamide → 1-(tert-butyl) 3-methyl 3-(N-methylformamido)pyrrolidine-1,3-dicarboxylate

HRID 1038096노트

반응식

HRID 1038096 반응식
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1([NH:19][CH:20]=[O:21])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1)=[O:6].[CH3:22]N(C=O)C.CI>C1COCC1>[CH3:3][O:4][C:5]([C:7]1([N:19]([CH:20]=[O:21])[CH3:22])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:8]1)=[O:6]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 576860951-(Tert-butyl) 3-methyl 3-formamidopyrrolidine-1,3-dicarboxylate

생성물 1

HCID 576862341-(tert-butyl) 3-methyl 3-(N-methylformamido)pyrrolidine-1,3-dicarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (60% in oil) (10 mg, 0.25 mmol) was added to a solution of 3-Formylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (2T) (50 mg, 0.183 mmol) in THF (3 ml). DMF (1 ml) was added and stirred for 1 hour. Methyl iodide (0.1 ml, 1.60 mmol) was added and the reaction was stirred overnight. The solvent was evaporated and the residue extracted with EtOAc (50 ml), washed with H2O (20 ml), dried over MgSO4, filtered and solvent evaporated yielding a residue which chromatographed on silica gel eluting with 3% MeOH/MeCl2 yielding 3T (50 mg, 94%). LCMS (MH 287) Retention time=2.77 minutes.

후처리

  1. stirringthe reaction was stirred overnight
  2. customThe solvent was evaporated
  3. extractionthe residue extracted with EtOAc (50 ml)
  4. washwashed with H2O (20 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvent evaporated
  8. customyielding a residue which
  9. customchromatographed on silica gel eluting with 3% MeOH/MeCl2 yielding 3T (50 mg, 94%)

출처 및 근거

ORD 기록
ord-4a9b17a89f5d4ff58c5313a12f182c1d
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546404B2

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