Methanol → (R)-Methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-3-(tert-butyldimethylsilyloxy)propanoate

HRID 1161222Notes

Reaction equation

HRID 1161222 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:25]([O-])=O)[C:16]1=[O:28])[C:11]([O:13][CH3:14])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO>[Pd]>[NH2:25][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[CH:23]=[CH:24][N:15]([C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:11]([O:13][CH3:14])=[O:12])[C:16]2=[O:28]

Participants

4

Reactant 2

HCID 887MethanolHCID 67088016(R)-Methyl 3-(tert-butyldimethylsilyloxy)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate

Product 1

HCID 67087826(R)-Methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-3-(tert-butyldimethylsilyloxy)propanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A round bottom flask was charged with (R)-methyl 3-(tert-butyldimethylsilyloxy)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanoate (5.5 g, 0.014 mol), methanol (100 mL, 2 mol) and palladium, 10% weight on charcoal (0.3 g, 0.003 mol) was added and the reaction stirred under hydrogen atmosphere (1 atm) for 2 h. The reaction was filtered over celite, the solvent was removed under reduced pressure and the residue purified by flash chromatography (40 g silica gel, 0-10% MeOH/DCM) to yield the product as a yellow sticky mass. MS m/z=377.5 (M+H).

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered over celite
  3. customthe solvent was removed under reduced pressure
  4. customthe residue purified by flash chromatography (40 g silica gel, 0-10% MeOH/DCM)
  5. customto yield the product as a yellow sticky mass

Sources & evidence

ORD record
ord-f690a6d13b2947b98a5eff845a57b7f6
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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