Chloroform → 4-(Pyridin-2-ylmethyl)-1,4-diaza-bicyclo[3.2.2]nonane

HRID 1454777Notes

Reaction equation

HRID 1454777 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[N:10]([C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=O)[CH2:9][CH2:8]2.C(Cl)(Cl)Cl.CO.C(Cl)(Cl)Cl>C1COCC1>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:16][N:10]1[CH:11]2[CH2:12][CH2:13][N:7]([CH2:15][CH2:14]2)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 21226445Aluminium lithium hydrideHCID 21584188Chloroform methanolHCID 68865039(1,4-Diazabicyclo[3.2.2]non-4-yl)(pyridin-2-yl)methanone

Product 1

HCID 114359054-(Pyridin-2-ylmethyl)-1,4-diaza-bicyclo[3.2.2]nonane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of lithium aluminum hydride (0.33 mL of 1M THF solution) at ambient temperature was added dropwise a solution of (1,4-diazabicyclo[3.2.2]non-4-yl)(pyridin-2-yl)methanone (120 mg, 0.52 mmol) in dry THF (2 mL). The resulting yellowish solution was stirred for 12 hours, quenched with water and aqueous NaOH, and filtered through diatomaceous earth. The filtrate was concentrated to give the product which was subjected to chromatography on silica gel eluting with an ammoniated-chloroform to 15% MeOH/chloroform gradient to give the title compound as a free base syrup (28.0 mg). MS (ES+) 218 (MH+).

Workup

  1. customquenched with water and aqueous NaOH
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated
  4. customto give the product which

Sources & evidence

ORD record
ord-840824c8338a4dec95a11e948ea5fdef
Source dataset
uspto-grants-2009_01
Patent number
US07482338B2

Reaction notes

Loading…