Tetrahydrofuran → HCID 10379719, compound

HRID 1461112Notes

Reaction equation

HRID 1461112 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1([CH3:26])[CH2:12][N:11]([CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10]1)#[N:8].O1CC[CH2:29][CH2:28]1>>[C:14]1([CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]2[CH2:10][C:9]([CH2:7][NH:8][CH2:28][CH3:29])([CH3:26])[CH2:12]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 100840771-Benzhydryl-3-methylazetidine-3-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 10379719HCID 10379719, compound

Procedure

6.1 g (161 mmol) of lithium aluminium hydride are suspended in 250 ml of tetrahydrofuran, and a solution of 21.1 g (80.5 mmol) of 3-cyano-1-diphenylmethyl-3-methylazetidine in 150 ml of tetrahydrofuran are added dropwise during 1 hour. The temperature is maintained during the addition at between 30° and 35° C. and the mixture is then stirred for 12 hours at room temperature. The excess lithium aluminium hydride is destroyed with ethanol, the insoluble inorganic fraction is filtered off, the tetrahydrofuran is removed, the residue is dissolved with chloroform, the organic phase is washed with water, dried with anhydrous sodium sulphate and evaporated to dryness and 16.1 g (75%) of 3-aminomethyl-1-diphenylmethyl-3-methylazetidine, melting point 46°-8° C., are obtained.

Workup

  1. temperatureThe temperature is maintained during the addition at between 30° and 35° C.
  2. customThe excess lithium aluminium hydride is destroyed with ethanol
  3. filtrationthe insoluble inorganic fraction is filtered off
  4. customthe tetrahydrofuran is removed
  5. dissolutionthe residue is dissolved with chloroform
  6. washthe organic phase is washed with water
  7. dry with materialdried with anhydrous sodium sulphate
  8. customevaporated to dryness and 16.1 g (75%) of 3-aminomethyl-1-diphenylmethyl-3-methylazetidine, melting point 46°-8° C.
  9. customare obtained

Sources & evidence

ORD record
ord-cb17a1e00b694e0a873a89dd77d03613
Source dataset
uspto-grants-1991_12
Patent number
US05073646

Reaction notes

Loading…