Potassium Carbonate → Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate

HRID 2196765Notes

Reaction equation

F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[O:13]1[C:17]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[O:13]1[C:17]2([CH2:22][CH2:21][N:20]([C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=3)[CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 4-fluorobenzoate (36.16 g, 215 mmol), 1,4-dioxa-8-azaspiro[4.5]decane (35.40 g, 247 mmol), and potassium carbonate (29.72 g, 215 mmol) were added to N,N-dimethylacetamide (500 mL) and heated to 100° C. for 16 hours. The solution was cooled, filtered, added to 2M HCl and extracted with 50% ethyl acetate (in hexanes). The organics were washed with water, brine, and dried on anhydrous sodium sulfate. The solution was concentrated and purified by flash column chromatography on silica gel with 20% ethyl acetate (in hexanes) increasing to 30% ethyl acetate (in hexanes).

Workup

temperatureThe solution was cooled
filtrationfiltered
additionadded to 2M HCl
extractionextracted with 50% ethyl acetate (in hexanes)
washThe organics were washed with water, brine
dry with materialdried on anhydrous sodium sulfate
concentrationThe solution was concentrated
custompurified by flash column chromatography on silica gel with 20% ethyl acetate (in hexanes)
temperatureincreasing to 30% ethyl acetate (in hexanes)

Sources & evidence

ORD record: ord-7b3c83d9ab3a4ffdac4d62625076cc37
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338466B2

Reaction notes

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