Sodium Bicarbonate → (S)-2-(3-oxocyclohexyl)isoindoline-1,3-dione

HRID 1050341Notes

Reaction equation

[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:3]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of 2-[(3R)-3-hydroxycyclohexyl]isoindoline-1,3-dione (3, 1.4 g, 5.71 mmol) in dichloromethane (50 mL) at 0° C., was added pyridinium chlorochromate (3.69 g, 17.12 mmol). The mixture was allowed to stir at 25° C. for 5 hours while monitoring by TLC. The reaction mixture was made basic (pH 8) with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (2×150 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to obtain 2-(3-oxocyclohexyl)isoindoline-1,3-dione (4) as a brown solid. Yield: 1.31 g, 94%; MS (ESI) m/z 244.15 [M+1]+.

Workup

extractionextracted with dichloromethane (2×150 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d2bb2a9b76104c24ae397824dbb7c947
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382248B2

Reaction notes

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