Hydrochloric Acid → 3-[2-(4-Chlorophenoxy)phenyl]-4-hydroxy-1-methylpyrrolidine-2-one
Reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]2[C:17](=[O:18])[CH2:16][N:15]([CH3:19])[C:14]2=[O:20])=[CH:4][CH:3]=1.[BH4-].[K+].[Cl-].[NH4+].Cl>O1CCCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]2[CH:17]([OH:18])[CH2:16][N:15]([CH3:19])[C:14]2=[O:20])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
5 g (15.8 mmol) of 3-[2-(4-chlorophenoxy)phenyl]-1-methylpyrrolidine-2,4-dione (compound IVb) was dissolved in a mixture of 150 mL of tetrahydrofuran and 15 mL of water. The solution was cooled to 0° C., and 4.3 g of potassium borohydride were added slowly, keeping the temperature below 10° C. The resulting solution was stirred at 0° C. for 6 hours. Then, a saturated solution of ammonium chloride was added, and the pH was adjusted to 3 with HCl 2 M. 100 mL of ethyl acetate were added. The organic phase was extracted, washed with saturated sodium bicarbonate and with water, dried and concentrated under vacuum, to obtain 4.5 g of 3-[2-(4-chlorophenoxy)phenyl]-4-hydroxy-1-methylpyrrolidine-2-one (compound XIIIb) as a sticky solid. Yield: 89.6%.
Workup
- customthe temperature below 10° C
- extractionThe organic phase was extracted
- washwashed with saturated sodium bicarbonate and with water
- customdried
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-d3b23bfebb624a09bb92814f10e4d986
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580972B2
Reaction notes
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