Ethanolamine → HCID 51890492, compound
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C@H:6]2[O:8][CH2:7]2)=[CH:4][CH:3]=1.[NH2:11][CH2:12][CH2:13][OH:14]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C@@H:6]([OH:8])[CH2:7][NH:11][CH2:12][CH2:13][OH:14])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 25 °C
Procedure
To (R)-4-chloro-styrene oxide (1.84 g, 11.9 mmol), 2-aminoethanol (2.18 g, 3.0 equivalents) was added. The mixture was stirred at 25° C. for 17 hours, to obtain the reaction mixture of the title compound (chemical purity: 70.9 area %). Ethyl acetate (5 mL) and saturated brine (5 mL) were added to the reaction mixture, and the organic layer and aqueous layer were separated. The obtained organic layer was washed twice with distilled water (5 mL), and was concentrated and dried under vacuum, to obtain 1.47 g of the title compound as viscous white solid. A solution consisting of ethyl acetate (4 mL) and hexane (10 mL) was added thereto under heating at 50° C., and the mixture was stirred for 1 hour and then cooled to 25° C. The resulting crystals were collected by filtration under reduced pressure, then washed with hexane (3 mL) and dried under vacuum, to obtain 993 mg of the title compound as white crystals (yield: 39%; chemical purity: 92.5 area %). The retention time in the chemical purity analysis method was 1.7 min.
Workup
- customto obtain
Sources & evidence
- ORD record
- ord-69226356ed014aa0bf08f75c0c99b5de
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273883B2
Reaction notes
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