Hydrochloric Acid → Arbaclofen
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][NH:11]C(=O)[C@H:9]2[C:14]([O:16]C)=[O:15])=[CH:4][CH:3]=1.Cl>ClC1C=CC=CC=1Cl>[NH2:11][CH2:12][C@@H:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:9][C:14]([OH:16])=[O:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Under a nitrogen atmosphere, methyl (3S,4R)-4-(4-chlorophenyl)-2-oxopyrrolidine-3-carboxylate (3.80 g, 15.0 mmol) was suspended in 1,2-dichlorobenzene (25 ml), and the suspension was poured into 6 mol/L hydrochloric acid (15.2 g). The mixture was reacted at 105° C. for 9 hours, then, cooled to 80° C. and the organic layer was separated by a liquid-separation operation. The aqueous layer was washed with 1,2-dichlorobenzene (11 ml), then, neutralized with a 20% sodium hydroxide aqueous solution to adjust pH to 7. The mixture was cooled to 15° C. and thermally insulated for 1 hour, then, the crystallized crystal was filtrated, and dried under reduces pressure, to obtain a title compound (2.69 g, 12.6 mmol)(yield: 84%). The optical purity of the resultant title compound was measured by HPLC to find a value of 99.9% ee or more (conditions are shown below).
Workup
- customThe mixture was reacted at 105° C. for 9 hours
- customthe organic layer was separated by a liquid-separation operation
- washThe aqueous layer was washed with 1,2-dichlorobenzene (11 ml)
- temperatureThe mixture was cooled to 15° C.
- filtrationthe crystallized crystal was filtrated
- customdried
Sources & evidence
- ORD record
- ord-6b3d82f665404b3ea0c9b711569b212c
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293926B2
Reaction notes
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