Reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[CH2:10][CH2:11][O:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CS(O)(=O)=O.[N-:21]=[N+]=[N-].[Na+].[OH-].[Na+]>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:15])[NH:21][CH2:10][CH2:11][O:12][C:13]=2[CH:14]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
7-tert-Butyl-chroman-4-one (1.3 g, 6.36 mmol) was taken up in dichloromethane (11.25 mL) and methane sulfonic acid (7.5 mL) and cooled to 0° C. With stirring at 0° C. was added sodium azide (827 mg, 2 eq) portion-wise. The resulting mixture was stirred at 0° C. for 3 hours and by TLC analysis there was no more starting material remaining, so the reaction mixture was poured into a 20% solution of NaOH(aq) (25 mL) at 0° C. This solution was stirred for 10 minutes and then it was extracted with dichloromethane (3×50 mL) and the combined dichloromethane layers were washed with brine (1×50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated. Purification by column chromatography on silica gel eluting with a gradient of 5% ethyl acetate in hexanes to 100% ethyl acetate afforded the title compound as a white solid (1.304 ) (M+H)+=220.
Workup
- stirringThe resulting mixture was stirred at 0° C. for 3 hours and by TLC analysis there
- stirringThis solution was stirred for 10 minutes
- extractionit was extracted with dichloromethane (3×50 mL)
- washthe combined dichloromethane layers were washed with brine (1×50 mL)
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customPurification by column chromatography on silica gel eluting with a gradient of 5% ethyl acetate in hexanes to 100% ethyl acetate
Sources & evidence
- ORD record
- ord-d3dd1bdac3da4e53b400e4d8daa62af4
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318719B2
Linked notes
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