N,N,N',N'-Tetramethylethylenediamine → Tert-butyl 2-hydroxy-2-(6-methoxypyridin-3-yl)ethyl(methyl)carbamate

HRID 23688

반응식

HRID 23688 반응식
[CH3:1][N:2]([CH3:10])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].CN(C)CCN(C)C.[CH3:19][O:20][C:21]1[N:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=1.[Cl-].[NH4+]>C1COCC1.C([Li])(CC)C>[OH:28][CH:27]([C:24]1[CH:25]=[N:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[CH2:1][N:2]([CH3:10])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

참가 물질

7

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 312724tert-butyl N,N-dimethylcarbamateHCID 33645766-Methoxypyridine-3-carbaldehyde

생성물 1

HCID 22574350Tert-butyl 2-hydroxy-2-(6-methoxypyridin-3-yl)ethyl(methyl)carbamate수율 42.5%

시약·촉매·용매 2

HCID 178418400CID 53628100촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl dimethylcarbamate (1.8 g, 0.012 mol) and tetramethylethylenediamine (2.6 g, 0.022 mol) in THF (anhydrous, 30 mL) was added sec-butyllithium (1.4 M in cyclohexane, 11 mL, 0.015 mmol) at −78° C. The mixture was stirred at that temperature for 30 minutes before a solution of 6-methoxy-3-pyridinecarboxaldehyde (J.Org.Chem. 55; 1; 1990; 69-73)(1.4 g, 0.01 mol, in 5 mL of dry THF) was introduced. The reaction mixture was stirred for 30 minutes, warmed to room temperature and stirred for 3 hours. Saturated ammonium chloride aqueous solution (20 mL) was added to quench the reaction after the reaction mixture was cooled to −78° C. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with brine and dried over sodium sulfate and concentrated. The residue was purified with a silica gel column to give the title compound (1.2 g) as a white solid.

후처리

  1. additionwas introduced
  2. stirringstirred for 3 hours
  3. customto quench
  4. customthe reaction after the reaction mixture
  5. temperaturewas cooled to −78° C
  6. customThe organic phase was separated
  7. extractionthe aqueous phase was extracted with dichloromethane
  8. washwashed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified with a silica gel column

출처 및 근거

ORD 기록
ord-52b78418d3a14c42bc535d0a0cefcfc5
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852731B2

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