Tetrahydrofuran → 3-Aminomethyl-1-benzhydrylazetidine

HRID 1294465Notes

Reaction equation

HRID 1294465 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 10.0 g (40 mmol) 1-diphenylmethyl-azetidin-3-carbonitrile in 20 ml abs. THF is added dropwise to a suspension of 3.1 g (80 mmol) lithium aluminium hydride in 80 ml abs. THF at RT and stirred overnight. The batch is carefully added to 2 ml ethanol and 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 CHCl3CH3OH/NH4OH (90/10/0 to 90/10/1). Yield: 5.6 g (55%) of slowly hardening resin.

Workup

  1. filtrationfiltered
  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 CHCl3CH3OH/NH4OH (90/10/0 to 90/10/1)

Sources & evidence

ORD record
ord-5be770c9b7b24fb48f5b623534eff417
Source dataset
uspto-grants-2007_07
Patent number
US07241745B2

Reaction notes

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