Tetrahydrofuran → 3-Aminomethyl-1-benzhydrylazetidine

HRID 1280784Notes

Reaction equation

HRID 1280784 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][CH:10]([C:12]#[N:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(O)C>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][CH:10]([CH2:12][NH2:13])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 100378743-Aminomethyl-1-benzhydrylazetidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10 g (40 mmol) 1-diphenylmethylazetidin-3-carbonitrile in 20 ml abs. THF are added dropwise at RT to a suspension of 3.1 g (80 mmol) lithium aluminum hydride in 80 ml abs. THF and stirred overnight, 2 ml ethanol are carefully added to the batch and the batch is filtered. The filtrate is concentrated under vacuum and dispersed between CHCl3 and water. The aqueous phase is extracted twice, each with 50 ml CHCl3, and the combined organic phases are dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH/NH4OH (90/10/0 to 90/10/1). Yield: 5.6 g (57%) of slowly solidifying resin.

Workup

  1. filtrationthe batch is filtered
  2. concentrationThe filtrate is concentrated under vacuum
  3. additiondispersed between CHCl3 and water
  4. extractionThe aqueous phase is extracted twice
  5. dry with materialeach with 50 ml CHCl3, and the combined organic phases are dried over sodium sulfate
  6. customthe solvent is removed under vacuum
  7. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH/NH4OH (90/10/0 to 90/10/1)

Sources & evidence

ORD record
ord-27192150f36747a8b02439ebaf9ce43e
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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