Furfural → 3-(4-Fur-2-ylmethylamino-1-oxoisoindolin-2-yl)-5-hydroxypiperidine-2,6-dione

HRID 891997Notes

Reaction equation

HRID 891997 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]1[CH2:17][CH:16]([OH:18])[C:15](=[O:19])[NH:14][C:13]1=[O:20])[C:6]2=[O:11].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH:26]=O.[BH4-].[Na+]>C(O)(=O)C>[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]1[CH2:17][CH:16]([OH:18])[C:15](=[O:19])[NH:14][C:13]1=[O:20])[C:6]2=[O:11]

Participants

5

Reactant 3

HCID 7362FurfuralHCID 4311764Sodium borohydrideHCID 99653763-(4-Amino-1-oxoisoindolin-2-yl)-5-hydroxypiperidine-2,6-dione

Product 1

HCID 222411783-(4-Fur-2-ylmethylamino-1-oxoisoindolin-2-yl)-5-hydroxypiperidine-2,6-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(4-amino-1-oxoisoindolin-2-yl)-5-hydroxypiperidine-2,6-dione (0.82 g, 3.0 mmol) and 2-furaldehyde (0.34 g, 3.5 mmol) in acetic acid (10 mL) is heated at reflux for 4 hours. To the mixture is added sodium borohydride (130 mg, 3.5 mmol) at room temperature and kept for 18 hours. The mixture is worked up to give 3-(4-fur-2-ylmethylamino-1-oxoisoindolin-2-yl)-5-hydroxypiperidine-2,6-dione which is further purified by column chromatography.

Workup

  1. temperatureat reflux for 4 hours

Sources & evidence

ORD record
ord-9d832ab939a84708930c2090ed664362
Source dataset
uspto-grants-2006_02
Patent number
US07005438B2

Reaction notes

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