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

HRID 252097

Reaction equation

HRID 252097 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 69888DiphenylsilaneSolvent

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-d625d7a84e184f3f81063df6e6a4c904
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Linked notes

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