Ethanol → (S)-tert-butyl 3-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate

HRID 418519Notes

Reaction equation

HRID 418519 reaction equation
[CH3:1][C:2]1[C:3]([N+:25]([O-])=O)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1)[CH:6]=[CH:5]2.C(O)C.[Cl-].[NH4+].O>[Fe]>[NH2:25][C:3]1[C:2]([CH3:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]([C@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1)[C:8]2=[O:12]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 66649026(S)-tert-butyl 3-(6-methyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate

Product 1

HCID 66649434(S)-tert-butyl 3-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

A round bottom flask was charged with (S)-tert-butyl 3-(6-methyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)pyrrolidine-1-carboxylate (500.0 mg, 0.001339 mol), ethanol (5 mL, 0.08 mol) and ammonium chloride (716.3 mg, 0.01339 mol) in water (3 mL, 0.2 mol) was added at 85° C. Iron (299 mg, 0.00536 mol) was added in portions and was stirred at that temperature for 30 minutes, poured onto methylene chloride (50 mL) and extracted. The solvent was removed under reduced pressure to afford the pure product as light yellow solid.

Workup

  1. additionwas added at 85° C
  2. additionpoured onto methylene chloride (50 mL)
  3. extractionextracted
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-90062f3493f24284acfaaf9e4fcb7380
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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