HCID 58636758, compound → HCID 58636757, compound

HRID 1158979Notes

Reaction equation

HRID 1158979 reaction equation
[C:1]([O:5][C:6](=[O:36])[N:7]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([CH2:34][OH:35])=[C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=2)[C:22]=1[CH3:23])[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6](=[O:36])[N:7]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([CH:34]=[O:35])=[C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=2)[C:22]=1[CH3:23])[C:8]1[CH:9]=[CH:10][C:11]([C:14]#[N:15])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58636758HCID 58636758, compound

Product 1

HCID 58636757HCID 58636757, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of [5-(3-cyano-benzyloxy)-6-hydroxymethyl-4-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (137) (235 mg, 0.484 mmol) and manganese (IV) dioxide (198 mg, 1.93 mmol) in methyl alcohol (5 mL) at room temperature for 2 hours. Excess manganese (IV) dioxide was filtered through a celite pad and washed with ethyl acetate. The filtrate was evaporated to give a crude residue, which was purified by column chromatography on silica gel using a gradient mixture of ethyl acetate:hexane (0:1 to 1:0) as eluant to give [5-(3-cyano-benzyloxy)-6-formyl-4-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (141) (154 mg, 66% yield) as a colorless solid.

Workup

  1. filtrationExcess manganese (IV) dioxide was filtered through a celite pad
  2. washwashed with ethyl acetate
  3. customThe filtrate was evaporated
  4. customto give a crude residue, which
  5. customwas purified by column chromatography on silica gel using
  6. additiona gradient mixture of ethyl acetate:hexane (0:1 to 1:0) as eluant

Sources & evidence

ORD record
ord-0347c87122214ecda48271f317a03080
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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