Sodium borohydride → 7-Amino-2-(4-tert-butyl-phenyl)-3-hydroxy-3-methyl-2,3-dihydro-isoindol-1-one

HRID 2251866Notes

Reaction equation

HRID 2251866 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21]([OH:23])([CH3:22])[C:20]3[C:15](=[C:16]([N+:24]([O-])=O)[CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:27])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4]>CO>[NH2:24][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[C:14](=[O:27])[N:13]([C:10]1[CH:11]=[CH:12][C:7]([C:3]([CH3:5])([CH3:4])[CH3:6])=[CH:8][CH:9]=1)[C:21]2([OH:23])[CH3:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 690317142-(4-Tert-butyl-phenyl)-3-hydroxy-3-methyl-7-nitro-2,3-dihydro-isoindol-1-one

Product 1

HCID 690306057-Amino-2-(4-tert-butyl-phenyl)-3-hydroxy-3-methyl-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (0.091 g, 2.36 mmol) was added in small portions to the mixture of 2-(4-tert-butyl-phenyl)-3-hydroxy-3-methyl-7-nitro-2,3-dihydro-isoindol-1-one (0.20 g, 0.59 mmol, Step H) and NiCl2.6H2O (0.28 g, 1.18 mmol) in 10 mL of MeOH at 0° C. over 30 min. The mixture was stirred at RT for 30 min, filtered through Celite®, and condensed. The titled compound was obtained as a white solid after flash column chromatography (0 to 25% of EtOAc in CH2Cl2). MS (ES+): 311.1 (M+H)+. Calc'd for C19H22N2O2-310.39.

Workup

  1. filtrationfiltered through Celite®, and condensed

Sources & evidence

ORD record
ord-a3702ef8b2f74ae1b3f5af547ee4a5d0
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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