(R)-3-phenylmorpholine Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

White to off-white Solid

(R)-3-phenylmorpholine Usage And Synthesis

Uses

(R)-3-Phenylmorpholine is used in the synthetic preparation of phosphoinositide kinase inhibitors.

Synthesis

General procedure: lithium aluminum hydride (3.55 g, 93.8 mmol) was added batchwise to a stirred solution of (R)-5-phenylmorpholin-3-one (4.15 g, 23.4 mmol) in anhydrous THF (30 mL) under the protection of nitrogen, keeping the reaction temperature at 0 °C. Subsequently, the reaction mixture was slowly warmed up to 45 °C and stirred continuously at this temperature for 5 hours. Upon completion of the reaction, the reaction was carefully quenched with saturated aqueous sodium sulfate solution. Ethyl acetate was added to the aqueous phase mixture and stirring was continued for 10 minutes. The resulting suspension was filtered through diatomaceous earth and the filtrate was collected and dried with anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the residue was dried well to give 615 mg of the target product 3-phenylmorpholine. The product was characterized by NMR (300 MHz, CDCl3): δ 3.00 (d, J = 11.4 Hz, 1H), 3.07-3.17 (m, 1H), 3.40 (t, J = 10.5 Hz, 1H), 3.62-3.70 (m, 1H), 3.80-3.95 (m, 3H), 7.27-7.41 (m, 5H).

References

[1] ACS Combinatorial Science, 2016, vol. 18, # 9, p. 569 - 574
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 15, p. 4316 - 4320
[3] Patent: WO2013/49719, 2013, A1. Location in patent: Paragraph 00183
[4] Patent: WO2018/116285, 2018, A1. Location in patent: Page/Page column 26-27

(R)-3-phenylmorpholine(74572-03-5)Related Product Information

• (S)-3-(tert-butyl)morpholine
• (R)-3-ISOPROPYLMORPHOLINE,
• (R)-3-(tert-butyl)morpholine
• (S)-3-Isopropylmorpholine
• (R)-3-((R)-sec-butyl)morpholine
• 3-ISOBUTYLMORPHOLINE
• (R)-3-Isobutylmorpholine
• (S)-3-Isobutylmorpholine
• 3-isopropylMorpholine
• OTAVA-BB 1055999
• 3-tert-Butyl-morpholine
• Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• (5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one
• (5R,6S)-5,6-Diphenyl-2-morpholinone
• Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• (5R)-N-(TERT-BUTOXYCARBONYL)-3,4,5,6-TETRAHYDRO-5-PHENYL-4(H)-1,4-OXAZIN-2-ONE
• (5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE