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

HRID 859878Notes

Reaction equation

HRID 859878 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 cooled on an ice bath, a diethyl ether solution (25 mL) of cis-1-benzyl-4-methyl-3-pyrrolidinecarbonitrile (4.11 g) was added dropwise and the mixture was stirred at room temperature for 1 hour. While the reaction mixture was cooled on an ice bath, a saturated aqueous solution of sodium hydrogen carbonate (8 mL) was carefully added dropwise. Following dilution with diethyl ether (100 mL), insoluble materials were collected by filtration and were washed with diethyl ether. The filtrate and the washing solution were combined and the combined solution was concentrated under reduced pressure. The resulting residue was purified on a silica gel column (hexane:ethyl acetate=1:1 shifted to ethyl acetate: methanol=10:1) to give 2.35 g of cis-1-benzyl-4-methyl-3-aminomethylpyrrolidine as a pale yellow oil.

Workup

  1. temperatureWhile the suspension was cooled on an ice bath
  2. temperatureWhile the reaction mixture was cooled on an ice bath
  3. filtrationwere collected by filtration
  4. washwere washed with diethyl ether
  5. concentrationthe combined solution was concentrated under reduced pressure
  6. customThe resulting residue was purified on a silica gel column (hexane:ethyl acetate=1:1 shifted to ethyl acetate: methanol=10:1)

Sources & evidence

ORD record
ord-8c7029ad0aef426497edcde90232950d
Source dataset
uspto-grants-2006_12
Patent number
US07153851B2

Reaction notes

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