Methanol → HCID 22485500, compound

HRID 2181302Notes

Reaction equation

HRID 2181302 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]([CH3:36])[C:15](=O)[CH2:16][CH:17]([N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[CH2:18][C:19]([N:21]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:22])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO>O1CCCC1>[CH2:23]([N:21]([CH3:22])[CH2:19][CH2:18][CH:17]([N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[CH2:16][CH2:15][N:14]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:36])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 22485515HCID 22485515, compound

Product 1

HCID 22485500HCID 22485500, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, lithium aluminum hydride (0.44 g, 12 mmol) was added to a solution of N,N′-dibenzyl-N,N′-dimethyl-3-(1-pyrrolidinyl)glutaramide (1.16 g, 2.85 mmol) in anhydrous tetrahydrofuran (20 mL) stirred in an ice bath, and the mixture was stirred at 65° C. for 2 hours. Methanol (3.0 mL, 74 mmol) was added to the ice-cold reaction mixture, and the ice bath was removed. Water (2.0 mL), diethyl ether (150 mL) and anhydrous magnesium sulfate (15 g) were added, and the mixture was stirred at room temperature for 1 hour. Insoluble materials were removed by filtration through Celite, an the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield N,N′-dibenzyl-N,N′-dimethyl-3-(1-pyrrolidinyl)-1,5-pentanediamine as a colorless oil (917.3 mg, yield: 85%).

Workup

  1. stirringthe mixture was stirred at 65° C. for 2 hours
  2. customthe ice bath was removed
  3. additionWater (2.0 mL), diethyl ether (150 mL) and anhydrous magnesium sulfate (15 g) were added
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. customInsoluble materials were removed by filtration through Celite
  6. concentrationan the filtrate was concentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4bee7fdb96b044fb818ad47ea123003b
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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