Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][O:6][C:7]2=[O:12].CN1CCOCC1.[C:20]12([CH2:30][C:31](Cl)=[O:32])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2>O1CCOCC1>[C:20]12([CH2:30][C:31]([NH:1][C:2]3[CH:11]=[CH:10][CH:9]=[C:8]4[C:3]=3[CH:4]=[CH:5][O:6][C:7]4=[O:12])=[O:32])[CH2:27][CH:26]3[CH2:25][CH:24]([CH2:23][CH:22]([CH2:28]3)[CH2:21]1)[CH2:29]2Participants
Procedure
To a solution of 5-amino-1H-isochromen-1-one (2.95 g, 18.3 mmol) and NMM (2.02 mL, 18.3 mmol) in 1,4 dioxane (55 mL) was added dropwise at room temperature a solution of 1-adamantaneacetic acid chloride (3.9 g, 18.3 mmol) in 1,4-dioxane (40 mL). The reaction mixture was stirred at room temperature for 3 h and then partitioned between DCM (400 mL) and water (200 mL). The layers were separated. The aqueous phase was washed with DCM (100 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was suspended in hexane (100 mL) and filtered off. The solid was collected on the filter and dried in vacuo to yield 2-adamantan-1-yl-N-(1-oxo-1H-isochromen-5-yl)-acetamide as a yellow solid (5.6 g, 16.7 mmol, 91%).
Workup
- custompartitioned between DCM (400 mL) and water (200 mL)
- customThe layers were separated
- washThe aqueous phase was washed with DCM (100 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- customevaporated
- filtrationfiltered off
- customThe solid was collected on the
- filtrationfilter
- customdried in vacuo
Sources & evidence
- ORD record
- ord-ab2f41996fd24e61be44dae0e8627aab
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07402596B2
Linked notes
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