Sodium Bicarbonate → 1-Benzyl-3-methylpyrrolidin-3-amine

HRID 252097

반응식

HRID 252097 반응식
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([NH:14]C(=O)C)([CH3:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C1([SiH2]C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([NH2:14])([CH3:13])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 13787481N-(1-benzyl-3-methylpyrrolidin-3-yl)acetamide

생성물 1

HCID 105118971-Benzyl-3-methylpyrrolidin-3-amine

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 69888Diphenylsilane용매

실험 절차

Add titanium (IV) isopropoxide (2.8 mL, 9.46 mmol) dropwise to a stirred mixture of N-(1-benzyl-3-methylpyrrolidin-3-yl)-acetamide (2 g, 8.6 mmol) and diphenylsilane (10 mL). Stir overnight at room temperature under nitrogen. Pour into saturated aqueous sodium hydrogen carbonate and extract with chloroform. Combine the organic layers and wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate. Add methanol and filter off the white precipitate. Add bulk Isolute sorbent SCX-2 silica (20 g) and stir for 2 h. Filter off the silica, wash with methanol and with 2 N ammonia in methanol. Concentrate to give 1-benzyl-3-methylpyrrolidin-3-ylamine which may be used in the next step without further purification (1.31 g, 86%). 1H NMR (300 MHz, CDCl3) δ 7.22-7.35 (5H, m), 3.59 (2H, d, J=2.26 Hz), 2.83 (1H, td, J=8.67, 5.27 Hz), 2.37-2.51 (2H, m), 2.30 (1H, d, J=9.04 Hz), 1.76-1.86 (1H, m), 1.66-1.74 (3H, m), 1.24 (3H, s), MS (ES): m/z=191 [M+H].

후처리

  1. extractionextract with chloroform
  2. washwash with saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. filtrationAdd methanol and filter off the white precipitate
  6. additionAdd bulk Isolute sorbent SCX-2 silica (20 g)
  7. stirringstir for 2 h
  8. filtrationFilter off the silica
  9. washwash with methanol and with 2 N ammonia in methanol
  10. concentrationConcentrate

출처 및 근거

ORD 기록
ord-d625d7a84e184f3f81063df6e6a4c904
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868014B2

연결된 노트

불러오는 중…