Butylamine → N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide
Reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14]C)=O)[CH2:4]1.[CH2:16]([NH2:20])[CH2:17][CH2:18][CH3:19]>>[CH2:16]([NH:20][C:12](=[O:14])[CH2:11][C@H:5]1[CH2:4][C@@H:3]([CH2:2][OH:1])[O:8][C:7]([CH3:9])([CH3:10])[O:6]1)[CH2:17][CH2:18][CH3:19]Participants
3
Procedure
A mixture of methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (110 grams) and n-butylamine (370 grams) was heated to reflux and stirred. After completion of the reaction, the reaction mixture was distilled under reduced pressure. Water (500 ml) was added to the obtained residue followed by sodium bicarbonate and washed it with petroleum ether. The reaction mixture was extracted into methylene chloride. The solvent from the reaction mixture was distilled off under reduced pressure to get the title compound.
Workup
- temperaturewas heated
- temperatureto reflux
- customAfter completion of the reaction
- distillationthe reaction mixture was distilled under reduced pressure
- additionWater (500 ml) was added to the obtained residue
- washwashed it with petroleum ether
- extractionThe reaction mixture was extracted into methylene chloride
- distillationThe solvent from the reaction mixture was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-2e393813214042aab9676ad8c8785296
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987444B2
Reaction notes
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