3,7-Dibenzyl-3,7-diazabicyclo[3.3.1]nonan-9-one → HCID 22490261, compound

HRID 2180009Notes

Reaction equation

HRID 2180009 reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[C:16](=[O:17])[CH:10]([CH2:11][N:12]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][Mg]Cl>C(OCC)C>[CH2:18]([N:12]1[CH2:11][CH:10]2[C:16]([OH:17])([CH3:25])[CH:14]([CH2:15][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)[CH2:13]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 3671723,7-Dibenzyl-3,7-diazabicyclo[3.3.1]nonan-9-oneHCID 178418332HCID 178418332, compound

Product 1

HCID 22490261HCID 22490261, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3,7-dibenzyl-3,7-diazabicyclo[3.3.1]nonane-9-one (from step (i) above; 2.05 g; 6.4 mmol) in diethyl ether (15 mL) was added to a stirred solution of methyl magnesium chloride (12.8 mmol) in diethyl ether (8 mL) over 80 minutes. The reaction mixture was subsequently stirred for 20 minutes and then quenched with HCl (1 M). The aqueous layer was separated, concentrated and partitioned between EtOAc and NaOH (2 M). The organic layer was separated and subsequently treated with ion exchange resin (Amberlyst IRA 400), the solvent removed and the residue subjected to column chromatography (hexane:EtOAc; 1:1 with NH3 sat. MeOH; gradient 0-32%) to give the sub-tide compound as a diastereoisomeric mixture in a 60% yield.

Workup

  1. customquenched with HCl (1 M)
  2. customThe aqueous layer was separated
  3. concentrationconcentrated
  4. custompartitioned between EtOAc and NaOH (2 M)
  5. customThe organic layer was separated
  6. additionsubsequently treated with ion exchange resin (Amberlyst IRA 400)
  7. customthe solvent removed
  8. customto give the sub-tide compound as a diastereoisomeric mixture in a 60% yield

Sources & evidence

ORD record
ord-4678e1db4a474c50af732ba16e1a0a8b
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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