Water → tert-butyl(+)-cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-ethanoate
Reaction equation
[H-].[Na+].Br[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:7][CH:6]=1.O.[CH3:25][N:26]([CH:28]=[O:29])C>>[CH:19]1([CH:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][N:26]3[CH2:25][C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[C:28]3=[O:29])=[CH:6][CH:7]=2)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:23][CH2:22][CH2:21][CH2:20]1Participants
Procedure
At 0° C., 611.3 mg (15.3 mmol, 60%) of sodium hydride were added to 2.035 g (15.3 mmol) of 1-oxoindoline in 12 ml of DMF. The mixture was stirred for 25 min, and 6.0 g (12.7 mmol, about 75% pure) of tert-butyl(+/−)-[4-(bromomethyl)phenyl](cyclopentyl)acetate were then added at 0° C. The reaction mixture was stirred for a further 4 h while slowly warming to RT, water was then added and the mixture was extracted twice with dichloromethane. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. In an ultrasonic bath, the crude product was treated with diethyl ether, and the solid was filtered off with suction and dried. This gave 3.40 g (65.2% of theory) of the target compound.
Workup
- stirringThe reaction mixture was stirred for a further 4 h
- extractionthe mixture was extracted twice with dichloromethane
- washThe combined organic phases were washed with saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- additionIn an ultrasonic bath, the crude product was treated with diethyl ether
- filtrationthe solid was filtered off with suction
- customdried
Sources & evidence
- ORD record
- ord-700136ea7c2a42ea8ab2a730d3c1533b
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642592B2
Reaction notes
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