Benzyl Alcohol → Benzyl oxolan-3-ylcarbamate

A mixture of 3-tetrahydrofuroic acid (3.5 gm, 30 mmol), diphenylphosphorylazide (6.82 ml, 32 mmol), triethylamine (5 ml, 36 mmol) in dioxane (35 ml) was stirred at room temperature for 20 minutes, then heated in a 100° C. oil bath under dry nitrogen for 2 hours. Benzyl alcohol (4.7 ml, 45 mmol) was then added, and heating was continued at 100° C. for 22 hours. The mixture was cooled, filtered, and filtrate concentrated under reduced pressure. The residue was dissolved in 2N HCl and extracted twice with ethyl acetate. The extracts were combined and washed with water, then sodium bicarbonate, and finally brine, and dried over magnesium sulfate. The product was concentrated under reduced pressure to an oil. The oil was chromatographed on silica gel, eluting with 30% to 60% ethyl acetate/hexanes, to give 3.4 g of N-benzyloxycarbonyl-3-aminotetrahydrofuran as an oil.

1. temperatureheated in a 100° C. oil bath under dry nitrogen for 2 hours
2. temperatureheating
3. waitwas continued at 100° C. for 22 hours
4. temperatureThe mixture was cooled
5. filtrationfiltered
6. concentrationfiltrate concentrated under reduced pressure
7. dissolutionThe residue was dissolved in 2N HCl
8. extractionextracted twice with ethyl acetate
9. washwashed with water
10. dry with materialsodium bicarbonate, and finally brine, and dried over magnesium sulfate
11. concentrationThe product was concentrated under reduced pressure to an oil
12. customThe oil was chromatographed on silica gel
13. washeluting with 30% to 60% ethyl acetate/hexanes

ORD record

ord-4f8b3a700af449b9af921a34e59c0cea

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696181B2