Butylamine → Ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate
Reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)=O.[CH2:17]([NH2:21])[CH2:18][CH2:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[CH2:17]([NH:21][CH2:1][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)[CH2:18][CH2:19][CH3:20]Participants
5
Procedure
To a solution of ethyl (4-formyl-2-methylphenoxy)acetate (3 g, 13.5 mmol) in anhydrous ethanol (50 mL) at room temperature, was added n-butylamine (1.6 mL, 16.2 mmol) and 4A molecular sieves. The resultant mixture was stirred at room temperature for 18 h under nitrogen, prior to portion wise addition of sodium triacetoxyborohydride (3.43 g, 16.2 mmol). After a further 3 h stirring at room temperature, the reaction was quenched by cautious addition of sat. sodium bicarbonate solution (40 mL) and then diluted with water (50 mL), before extracting with EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4) and the solvents removed in vacuo, to afford the title compound as brown oil (2.6 g).
Workup
- customthe reaction was quenched by cautious addition of sat. sodium bicarbonate solution (40 mL)
- additiondiluted with water (50 mL)
- extractionbefore extracting with EtOAc (2×100 mL)
- dry with materialThe combined organic extracts were dried (MgSO4)
- customthe solvents removed in vacuo
Sources & evidence
- ORD record
- ord-b84e7ef73b164e4cb7221d2f1da49fde
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199239B2
Reaction notes
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