Methanol → HCID 22479129, compound

HRID 1392161Notes

Reaction equation

HRID 1392161 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:34]=[CH:33][C:12]([CH2:13][C:14]23[C:22](=[O:23])[N:21]([C:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=4)[C:20](=[O:32])N2C[CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=1)=[O:2].[C-:35]#[N:36].[Na+].[CH3:38][OH:39]>O=[Mn]=O>[CH3:38][O:39][C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]23[C:22](=[O:23])[N:21]([C:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=4)[C:20](=[O:32])[N:36]2[CH2:35][CH2:17][CH2:16][CH2:15]3)=[CH:33][CH:34]=1)=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 22479142HCID 22479142, compound

Product 1

HCID 22479129HCID 22479129, compound

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

To a solution of 6-[4-(2-formylphenyl)benzyl]-8-(3,5-dichlorophenyl)-1,8-diazabicyclo[4.3.0]nonane-7,9-dione (0.206 g) in MeOH (20 mL) was added NaCN (0.204 g), ACOH (0.086 mL) and MnO2 (activated, 1.84 g) and the mixture was stirred overnight at room temperature. The inorganics were removed by filtration through Celite and the filtrate was evaporated. The residue was dissolved in EtOAc and washed with water, brine, dried (MgSO4), filtered, and concentrated. Purification by chromatography (Silica gel: EtOAc/hexane: 1/2) afforded the titled compound (0.161 g). It was converted to the HCl salt. MS (m/z) 545 (M30 +Na), 523 (MH+)

Workup

  1. customThe inorganics were removed by filtration through Celite
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (Silica gel: EtOAc/hexane: 1/2)

Sources & evidence

ORD record
ord-eab4c6dd3f1c4813bf6527e0e7fe351f
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

Loading…