Benzylethanolamine → HCID 178499151, compound
Reaction equation
[CH:1]([C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])=O.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH2:19]([NH:26][CH2:27][CH2:28][OH:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O>[CH2:19]([N:26]([CH2:1][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])[CH2:27][CH2:28][OH:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
Methyl 4-formyl-1H-imidazole-5-carboxylate (1.68 mmol, 1 equiv.) was taken up in dry THF (10 ml). Dry Na2SO4 (15.53 mmol, 9.2 equiv.) and N-benzylethanolamine (1.99 mmol, 1.18 equiv.) were added, and the mixture was stirred for 1 h at 25° C. under nitrogen. NaBH(OAc)3 (2.36 mmol, 1.4 equiv.) was then added in portions, and the reaction mixture was stirred for 16 h. Then water (5 ml) was added, and the mixture was neutralised with sat. NaHCO3 solution (10 ml). Extraction with DCM (2×20 ml) was carried out, and the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, 5-10% MeOH in DCM), and the desired product was thus obtained in the form of a white solid. Yield: 99%
Workup
- stirringthe reaction mixture was stirred for 16 h
- extractionExtraction with DCM (2×20 ml)
- dry with materialthe combined organic phases were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting crude product was purified by column chromatography (silica gel, 5-10% MeOH in DCM)
Sources & evidence
- ORD record
- ord-2199dc5a437048fbab7dbe0aa070d566
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357717B2
Reaction notes
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