Ethyl Acetate → (6-methoxy-3,4-dihydro-2H-1-oxa-5,9-diaza-phenanthren-3-yl)-methanol

HRID 633796Notes

Reaction equation

HRID 633796 reaction equation
[BH4-].[Na+].C[O:4][C:5]([C:7]1[CH2:8][O:9][C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[CH:20]=1)=[N:17][C:16]([O:21][CH3:22])=[CH:15][CH:14]=3)=O.[Cl-].[Li+].C(OCC)(=O)C>CO.[Pd]>[CH3:22][O:21][C:16]1[N:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]1[O:9][CH2:8][CH:7]([CH2:5][OH:4])[CH2:20][C:19]2=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 711187386-methoxy-2H-1-oxa-5,9-diaza-phenanthrene-3-carboxylic acid methyl ester

Product 1

HCID 71117945(6-methoxy-3,4-dihydro-2H-1-oxa-5,9-diaza-phenanthren-3-yl)-methanolYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Sodium borohydride (417 mg, 11.03 mmol, 5.0 eq) is added at 0° C. to a stirred suspension of 6-methoxy-2H-1-oxa-5,9-diaza-phenanthrene-3-carboxylic acid methyl ester (600 mg, 2.20 mmol, 1.0 eq) in methanol (60 mL), followed by lithium chloride (467 mg, 11.03 mmol, 5.0 eq). After 3 hours stirring at room temperature, solvent is removed and the residue is dissolved in methanol (60 mL) and treated with 10% palladium on activated carbon (100 mg, 0.09 mmol, 0.05 eq). The resulting mixture is stirred under hydrogen flow (3 bars) at room temperature for 3 hours. The catalyst is then removed by filtration and the solution is concentrated to give a residue that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 4:1 to 3:1, v/v) to afford (6-methoxy-3,4-dihydro-2H-1-oxa-5,9-diaza-phenanthren-3-yl)-methanol as a white solid (400 mg, 74% yield).

Workup

  1. customsolvent is removed
  2. dissolutionthe residue is dissolved in methanol (60 mL)
  3. stirringThe resulting mixture is stirred under hydrogen flow (3 bars) at room temperature for 3 hours
  4. customThe catalyst is then removed by filtration
  5. concentrationthe solution is concentrated
  6. customto give a residue that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-98d59702339a41b892c686e9311591c4
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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