Triphenylphosphine → HCID 22107101, compound

A mixture of the compound prepared as described in Example 4 (3.612 g), triphenylphosphine (6.759 g), and 1-(4-hydroxyphenyl)-6-phenylhexane (6.555 g) in tetrahydrofuran (32 ml) was cooled to approximately 1°-2° C., and treated with a solution of diethylazodicarboxylate (4.080 g) in tetrahydrofuran (10 ml) over a seventeen minute period. After the addition was complete, the reaction suspension was allowed to warm to room temperature. After about 24 hours, the resulting brown solution was concentrated in vacuo. The residue was diluted with chloroform (10 ml), the insoluble material removed by filtration, and the filtrate concentrated in vacuo. The material was dissolved in methylene chloride and 230-400 mesh silica gel (36 g) was added. The mixture was concentrated in vacuo to a powder. The mixture was subjected to flash silica gel chromatography, eluting with hexane/ethyl acetate (5:2, 10×100 ml), then hexane/ethyl acetate (5:3, 7×100 ml, 1×200 ml), next ethyl ether (10×200 ml) and finally ethyl acetate (2×200 ml, 2×500 ml). The fractions containing the desired material were concentrated in vacuo to give a gold oil. The gold oil was dissolved in methylene chloride (24 ml) and purified by preparative centrifugal thin-layer chromatography (4mm plate, flow rate=8 ml/min), eluting with 50% ethyl acetate/hexane until the first band elutes then solvent switched to ethyl acetate. The fractions containing methyl 3-[4-(6-hexylphenyl)phenoxy]-2-pyrrolidone-5-carboxylate were combined and concentrated in vacuo to give a gold oil. The oil was dissolved in diethyl ether (10 ml). Hexane was added until the solution became turbid. After forty five minutes at room temperature, the turbid solution was concentrated in vacuo resulting in the formation of a solid material. Diethyl ether (10 ml) was added to the material, then the insolubles were collected by filtration. The filtrate was concentrated in vacuo to give an oil that crystallizes out. Diethyl ether was added to the crystalline material. The resulting suspension was rigorously stirred for thirty minutes. Insolubles were collected by filtration to give 3.91 g of methyl 3-(4-(6-hexylphenyl)phenoxy]-2-pyrrolidone-5-carboxylate.

1. additionA mixture of the compound
2. customprepared
3. temperaturewas cooled to approximately 1°-2° C.
4. additionAfter the addition
5. concentrationthe resulting brown solution was concentrated in vacuo
6. additionThe residue was diluted with chloroform (10 ml)
7. customthe insoluble material removed by filtration
8. concentrationthe filtrate concentrated in vacuo
9. dissolutionThe material was dissolved in methylene chloride
10. addition230-400 mesh silica gel (36 g) was added
11. concentrationThe mixture was concentrated in vacuo to a powder
12. washeluting with hexane/ethyl acetate (5:2, 10×100 ml)
13. additionThe fractions containing the desired material
14. concentrationwere concentrated in vacuo
15. customto give a gold oil
16. custompurified by preparative centrifugal thin-layer chromatography (4mm plate, flow rate=8 ml/min)
17. washeluting with 50% ethyl acetate/hexane until the first band elutes
18. additionThe fractions containing methyl 3-[4-(6-hexylphenyl)phenoxy]-2-pyrrolidone-5-carboxylate
19. concentrationconcentrated in vacuo
20. customto give a gold oil
21. waitAfter forty five minutes at room temperature
22. concentrationthe turbid solution was concentrated in vacuo
23. customresulting in the formation of a solid material
24. filtrationthe insolubles were collected by filtration
25. concentrationThe filtrate was concentrated in vacuo
26. customto give an oil that
27. customcrystallizes out
28. additionDiethyl ether was added to the crystalline material
29. filtrationInsolubles were collected by filtration

ORD record

ord-bfaafc89c7814d1a9bc8f5d88ac77c7c

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05576323