1-Amino-2-propanol → 1-((2-Hydroxyethyl)(methyl)amino)-3-(1-nitrocyclohexyl)propan-2-ol
Reaction equation
[O:1]1[CH2:3][CH2:2]1.CC([CH2:7][NH2:8])O.[N+:9]([C:12]1([CH2:18][CH:19]2[CH2:21][O:20]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:11])=[O:10]>>[OH:1][CH2:2][CH2:3][N:8]([CH3:7])[CH2:21][CH:19]([OH:20])[CH2:18][C:12]1([N+:9]([O-:11])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1Participants
Procedure
A one neck 100 mL round bottom flask equipped with a stir bar, condenser and nitrogen outlet is charged with 3.24 g (34.6% purity, 0.018 mols) of 24(1-nitrocyclohexyl)methyl)oxirane and 1.31 g (0.018 mols) of monomethylethanolamine. The reaction mixture is stirred at room temperature for 30 minutes followed by heating at 40° C. for 1.5 h. The yellow color oxirane turns to dark orange and the resulting product has high viscosity. GC of the reaction mixture after this time still shows the presence of the epoxide. At this point, 0.7 mL (0.65 g) of additional monomethylethanolamine is added and stirred for additional 1.5 h at 40° C. and overnight at room temperature. GC analysis of the resulting mixture shows the nitro epoxide (12) is fully consumed. At this point, the reaction is deemed complete. Compound (13), 1-((2-hydroxyethyl)(methyl)amino)-3-(1-nitrocyclohexyl)propan-2-ol was identified by LC/MS with [M+H]=261.17. The product mixture from the epoxy ring opening step is used as-is for the hydrogenation step.
Workup
- customA one neck 100 mL round bottom flask equipped with a stir bar, condenser and nitrogen outlet
- temperatureby heating at 40° C. for 1.5 h
- stirringstirred for additional 1.5 h at 40° C. and overnight at room temperature
- customis fully consumed
Sources & evidence
- ORD record
- ord-5a74f53537ac4aa5b1de56d3a0bb78b3
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08480800B2
Reaction notes
Loading…