Acetone → 1-[(2,3-Dihydroxypropyl)amino]-6-methoxy-4-phenylisoquinoline-3-carbonitrile

HRID 639892Notes

Reaction equation

HRID 639892 reaction equation
C([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:7]([C:23]#[N:24])[N:6]=1)C=C.[CH3:25][C:26]([CH3:28])=[O:27].C[N+]1([O-])CC[O:33]CC1.[O-]S([O-])=O.[Na+].[Na+]>C(=O)(O)[O-].[Na+].O=[Os](=O)(=O)=O.O>[OH:27][CH:26]([CH2:28][OH:33])[CH2:25][NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:7]([C:23]#[N:24])[N:6]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 11358963(Allylamino)-6-methoxy-4-phenylisoquinoline-3-carbonitrile

Product 1

HCID 111988731-[(2,3-Dihydroxypropyl)amino]-6-methoxy-4-phenylisoquinoline-3-carbonitrile

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 95 mg of (allylamino)-6-methoxy-4-phenylisoquinoline-3-carbonitrile in 9 ml, acetone and 3.5 mL water were added 0.36 ml OsO4 soln (2.5% in 2-Me-2-propanol) and 42 mg of NMO. The reaction was stirred at room temp for 19 h, then diluted with 1:1 saturated aqueous sodium bicarbonate:saturated aqueous Na2SO3. The mixture was partitioned between EA and saturated aqueous sodium bicarbonate, and the organic solution was washed once with brine. The combined aqueous solution were extracted once with EtOAc. The combined organic solutions were dried (Na2SO4) and concentrated. Flash chromatography (0-4% MeOH(10% NH4OH)/EA, 40 g silica) gave a tan solid.

Workup

  1. customThe mixture was partitioned between EA and saturated aqueous sodium bicarbonate
  2. washthe organic solution was washed once with brine
  3. extractionThe combined aqueous solution were extracted once with EtOAc
  4. dry with materialThe combined organic solutions were dried (Na2SO4)
  5. concentrationconcentrated
  6. customFlash chromatography (0-4% MeOH(10% NH4OH)/EA, 40 g silica) gave a tan solid

Sources & evidence

ORD record
ord-91569bb5e0444f698492ba74fa590a7c
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

Loading…