tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

Chemical Properties

tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is Off-white Solid

Uses

Tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is a reactant used in the preparation of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G and colla gen cross-link pyridinolines.

Uses

(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester is a reactant used in the preparation of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G and collagen cross-link pyridinolines.

Synthesis

N-Boc-substituted diphenylamino alcohol (1.9 g, 4.2 mmol) was dissolved in toluene (25 mL), p-TsOH (p-TsOH, 70 mg, 0.42 mmol) was added, and the reaction was heated and refluxed at 120 °C overnight. Upon completion of the reaction, it was cooled to room temperature and a solid was precipitated. The solid was collected by filtration, washed with saturated aqueous sodium chloride solution, the organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The yellow solid obtained was recrystallized by anhydrous ethanol (20 mL) to give a white solid. After filtration and drying by rotary evaporation, 1.22 g (2R,3S)-N-tert-butoxycarbonyl-2,3-diphenylmorpholin-6-one was obtained as a white solid in 85% yield.

References

[1] Patent: CN104945345, 2017, B. Location in patent: Paragraph 0105; 0107; 0116; 0118
[2] Journal of the American Chemical Society, 1988, vol. 110, # 5, p. 1547 - 1557
[3] Synlett, 2005, # 4, p. 693 - 696
[4] Organic Syntheses, 2003, vol. 80, p. 18 - 30