2-(3-Oxobutyl)isoindoline-1,3-dione → HCID 68776028, compound

HRID 1711195Notes

Reaction equation

HRID 1711195 reaction equation
[C:1]1([N:7]2[CH2:11][C@@H:10]([CH2:12][CH2:13][CH3:14])[N:9]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:8]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:23]([CH3:37])[CH2:24][CH2:25][N:26]1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=[O:36].[BH3-]C#N.[Na+]>CC(O)=O.CO>[O:21]=[C:8]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][C@@H:10]([CH2:12][CH2:13][CH3:14])[N:9]1[CH:15]1[CH2:20][CH2:19][N:18]([CH:23]([CH3:37])[CH2:24][CH2:25][N:26]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dioneHCID 5003444Sodium cyanoborohydrideHCID 68775209HCID 68775209, compound

Product 1

HCID 68776028HCID 68776028, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

Following general procedure B: a solution of (R)-1-phenyl-3-piperidin-4-yl-4-propyl-imidazolidin-2-one (152 mg, 0.53 mmol), 2-(3-oxo-butyl)-isoindole-1,3-dione (230 mg, 1.06 mmol), NaBH3CN (108 mg, 1.72 mmol) and glacial AcOH (8 drops) in MeOH (2.5 ml) was stirred at 60° C. for 16.5 hours. Standard workup and purification by flash column chromatography on silica (CH2Cl2/MeOH, 29:1) gave 2-{3-[4-((R)-2-oxo-3-phenyl-5-propyl-imidazolidin-1-yl)-piperidin-1-yl]-butyl}-isoindole-1,3-dione, contaminated with alcohol resulting from reduction of excess ketone (302 mg).

Workup

  1. customStandard workup and purification by flash column chromatography on silica (CH2Cl2/MeOH, 29:1)

Sources & evidence

ORD record
ord-9d2b8ccaa87e4f46becc095365be7990
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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