Furfural → HCID 22241190, compound

HRID 989796Notes

Reaction equation

HRID 989796 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:21])[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:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH:27]=O.[BH4-].[Na+]>C(O)(=O)C>[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:21])[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 9922018460741-57-5

Product 1

HCID 22241190HCID 22241190, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(4-amino-1,3-dioxoisoindolin-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 this mixture is maintained for 18 hours. The mixture is worked up to give 3-(4-fur-2-ylmethylamino-1,3-dioxoisoindolin-2-yl)-5-hydroxypiperidine-2,6-dione which is further purified by column chromatography.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturethis mixture is maintained for 18 hours

Sources & evidence

ORD record
ord-4943872f93b24837bef7c550cac848a8
Source dataset
uspto-grants-2002_10
Patent number
US06458810B1

Reaction notes

Loading…