Reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:13]([N:15]([C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=1)[CH2:16][CH2:17][NH2:18])[CH3:14].[BH4-].[Na+].O>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:18][CH2:17][CH2:16][N:15]([CH2:13][CH3:14])[C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
1.62 g (10 mmol) of 4-tert-butyl benzaldehyde and 1.78 g (10 mmol) of N*1*-ethyl-N*1* -m-tolyl-ethane-1,2-diamine were dissolved in 20 ml methanol and the solution was stirred for 2 h at rt. 567 mg (15 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt over night. Water was added and the solvent was evaporated. The reaction mixture was extracted with diethyl ether and the organic layer was washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave the 3.08 g (95%) product as a light yellow oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.33 (d, 2H), 7.24 (d, 2H), 7.09 (dd, 1H), 6.51 (m, 3H), 3.78 (s, 2H), 3.42 (t, 2H), 3.34 (q, 2H), 2.85 (t, 2H), 2.29 (s, 3H), 1.31 (s, 9H), 1.11 (t, 3H).
Workup
- stirringThe reaction mixture was stirred at rt over night
- customthe solvent was evaporated
- extractionThe reaction mixture was extracted with diethyl ether
- washthe organic layer was washed with saturated aqueous NaCl solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-f8163ec0f6c446e3a9d9efb6fbe68099
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259183B2
Linked notes
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