Sodium Bicarbonate → cis-1-Benzyl-4-methyl-3-aminomethylpyrrolidine

HRID 424721Notes

Reaction equation

HRID 424721 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:18][C@H:17]([CH3:19])[C@H:16]([C:20]#[N:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)(O)[O-].[Na+]>C(OCC)C>[CH2:7]([N:14]1[CH2:18][C@H:17]([CH3:19])[C@H:16]([CH2:20][NH2:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 66704969cis-1-Benzyl-4-methyl-3-pyrrolidinecarbonitrile

Product 1

HCID 15206166cis-1-Benzyl-4-methyl-3-aminomethylpyrrolidineYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Lithium aluminum hydride (80%, 3.89 g) was suspended in diethyl ether (90 mL). While the suspension was chilled in an ice bath, cis-1-benzyl-4-methyl-3-pyrrolidinecarbonitrile (4.11 g) in diethyl ether (25 mL) was added dropwise and the mixture was stirred at room temperature for 1 hour. Subsequently, a saturated aqueous solution of sodium bicarbonate (8 mL) was carefully added dropwise while the reaction mixture was chilled in an ice water bath. The reaction mixture was then diluted with diethyl ether (100 mL) and the insoluble material was filtered and was washed with diethyl ether. The filtrate and the washings were combined and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1->ethyl acetate:methanol=10:1) to give cis-1-benzyl-4-methyl-3-aminomethylpyrrolidine as a pale yellow oil (2.35 g).

Workup

  1. temperatureWhile the suspension was chilled in an ice bath
  2. temperaturewas chilled in an ice water bath
  3. filtrationthe insoluble material was filtered
  4. washwas washed with diethyl ether
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1->ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-248178d2936c43b6b270c2910856af95
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

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