Hydroxyamine hydrochloride → HCID 86607058, compound

Intermediate (b) N-BOC-(R)-2-(3-formyl-4-hydroxybenzyl)morpholine (0.192 g, 0.06 mmol) was dissolved in dry acetone (5 mL) with potassium carbonate (0.165 g, 1.19 mmol), under an atmosphere of nitrogen and iodomethane (0.074 mL, 1.19 mmol) added in one portion. The resulting mixture was stirred at room temperature for 18 hrs and then concentrated in vacuo. The residue was dissolved in water (10 mL) and extracted with diethyl ether (10 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The orange oil was purified by column chromatography (silica; 35% ethyl acetate/isohexane) to yield the desired product as a yellow oil (0.157 g, 78%). The material was used directly in the next step. N-BOC-(R)-2-(3-formyl-4-methoxybenzyl)morpholine (0.157 g, 0.468 mmol) was dissolved in ethanol (5 mL) and added to a solution of hydroxylamine hydrochloride (42 mg, 0.61 mmol) and sodium acetate (88 mg, 1.08 mmol) in ethanol (5 mL) at room temperature. The resulting mixture was stirred at room temperature for 18 hrs and then heated at 80° C. for 72 hrs. The reaction mixture was diluted with water (40 mL) and extracted with ethyl acetate (20 mL×2). Combined organic layers were washed with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo to yield the desired intermediate (a), N-BOC-(R)-2-(3-hydroxyimino-4-methoxybenzyl)morpholine as a yellow oil (85 mg).

1. temperatureheated at 80° C. for 72 hrs
2. extractionextracted with ethyl acetate (20 mL×2)
3. washCombined organic layers were washed with brine (10 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-4c57ad26a7224223b38256462989cb9d

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323466B2