Sodium Bicarbonate → HCID 86679269, compound

1,4-Oxazepane hydrochloride (1.0 g) and TEA (1.1 mL) were added to a chloroform (20 mL) solution of 4-ethynylbenzaldehyde (1.0 g) obtained by the same method as the synthesis method described in the literature (Tetrahedron Letters, 2007, Vol. 48(33), pp. 5817-5820). The mixture was stirred for 30 minutes at room temperature, and acetic acid (0.45 mL) was added, followed by stirring the mixture for 1 hour at room temperature. Then, sodium triacetoxyborohydride (2.4 g) was added, and the mixture was stirred for 15 hours at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and then the mixture was extracted with chloroform. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by NH type silica gel chromatography (gradient elution with hexane/ethyl acetate=90/10→60/40) to obtain 4-(4-ethynylbenzyl)-1,4-oxazepane (yellow solid) (1.4 g, 87%).

1. customobtained by the same method as the synthesis method
2. stirringby stirring the mixture for 1 hour at room temperature
3. stirringthe mixture was stirred for 15 hours at room temperature
4. extractionthe mixture was extracted with chloroform
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationThen, the desiccant was filtered out
8. distillationthe solvent was distilled off under reduced pressure
9. customThe resulting residue was purified by NH type silica gel chromatography (gradient elution with hexane/ethyl acetate=90/10→60/40)

ORD record

ord-5ac7ebb3b6594191892e20445842458e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073821B2