Sodium Hydroxide → HCID 117718459, compound
Reaction equation
[CH2:1]([CH:3]([CH2:16][CH3:17])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]=O)[CH:9]=[C:10]([CH:13]=1)[CH:11]=O)[CH3:2].[NH2:18][CH2:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH:28]([CH3:30])[CH3:29].[BH4-].[Na+].[OH-].[Na+]>CCOC(C)=O.CO>[CH2:1]([CH:3]([CH2:16][CH3:17])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:14][NH:18][CH2:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH:9]=[C:10]([CH2:11][NH:18][CH2:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH:13]=1)[CH3:2]Participants
Procedure
5-(2-Ethylbutoxyl)isophthalaldehyde (0.20 g, 0.88 mmol) and MeOH (15 mL) were added to a round-bottom flask. To the solution was added N1-(3-aminopropyl)-N3-isobutylpropane-1,3-diamine (0.33 g, 1.76 mmol) and the reaction mixture was stirred for 24 h. Sodium borohydride (0.13 g, 3.52 mmol) was added and the reaction mixture stirred for 1 h. The reaction mixture was concentrated under reduced pressure to afford a white solid. Aqueous NaOH (10%, 50 mL) and EtOAc (50 mL) were added and the reaction mixture stirred for 1 h. The layers were separated and the aqueous layer was extracted with EtOAc (50 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product a clear oil.
Workup
- stirringthe reaction mixture stirred for 1 h
- concentrationThe reaction mixture was concentrated under reduced pressure
- customto afford a white solid
- stirringthe reaction mixture stirred for 1 h
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (50 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-661e34d7ed8243af96827e5e01f17a53
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09439433B2
Reaction notes
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