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

HRID 252097

反応式

HRID 252097 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 69888Diphenylsilane溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-d625d7a84e184f3f81063df6e6a4c904
出典データセット
uspto-grants-2011_01
特許番号
US07868014B2

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