N,N,N',N'-Tetramethylethylenediamine → Tert-butyl 2-phenylpyrrolidine-1-carboxylate

HRID 321950노트

반응식

HRID 321950 반응식
CN(C)CCN(C)C.[Li]CCCC.[C:14]([N:21]([CH2:29][CH2:30][CH2:31]Cl)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>C1COCC1>[C:17]([O:16][C:14]([N:21]1[CH2:29][CH2:30][CH2:31][CH:22]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

참가 물질

5

반응물 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 11098062N-Boc-N-benzyl-3-chloropropylamineHCID 178418339Butyllithium

생성물 1

HCID 3772557Tert-butyl 2-phenylpyrrolidine-1-carboxylate수율 65.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield).

후처리

  1. customThe reaction mixture was then quenched with aqueous NH4Cl (20 mL)
  2. additiondiluted with Et2O (150 mL)
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted twice with Et2O
  5. washThe combined organic phases were washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-14bd27733a164910a2ebc08fa2747b84
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211170B1

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