N-Methylallylamine → (2R)-1-[allyl(methyl)amino]propan-2-ol
Reaction equation
[CH3:1][C@@H:2]1[CH2:4][O:3]1.[CH3:5][NH:6][CH2:7][CH:8]=[CH2:9].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>O1CCOCC1>[CH2:7]([N:6]([CH3:5])[CH2:4][C@H:2]([OH:3])[CH3:1])[CH:8]=[CH2:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
(2R)-2-methyloxirane (13.76 g) was added to a suspension of N-methylprop-2-en-1-amine (25 ml) and ytterbium(III) trifluoromethanesulfonate (100 mg) in dioxane (100 ml) and heated to 140° C. for 1 hour under microwave irradiation. The solution was concentrated in vacuo and the residue partitioned between water (100 ml) and ethyl acetate (200 ml). The organic extract was dried and solvent removed in vacuo yielding (2R)-1-[allyl(methyl)amino]propan-2-ol as a yellow oil (8.8 g, 29%); NMR spectrum (CDCl3) 1.20 (d, 3H), 2.33 (s, 3H), 2.27-2.46 (m, 2H), 3.05 (m, 1H), 3.23 (m, 1H), 3.88 (m, 1H), 5.19-5.29 (m, 2H), 5.90 (m, 1H); Mass spectrum M+ 129.
Workup
- concentrationThe solution was concentrated in vacuo
- customthe residue partitioned between water (100 ml) and ethyl acetate (200 ml)
- extractionThe organic extract
- customwas dried
- customsolvent removed in vacuo
Sources & evidence
- ORD record
- ord-5c9a8c5125bc4509b8e1f1637f11c857
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625908B2
Reaction notes
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