Morpholine → (1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanol

(1S,2S)-2-Amino-3-morpholino-1-phenyl-1-propanol was prepared in the same manner as in Example 11, except that morpholine was used in place of N-methylpiperazine. The compound obtained (99.2 mg, 0.42 mmol) was dissolved in methylene chloride, 2-hydroxy-n-octanoic acid (80.0 mg, 0.50 mmol) and N-hydroxysuccinimide (102.1 mg, 0.42 mmol) were added thereto at room temperature, and then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (118.1 mg, 0.62 mmol) was added thereto under ice cooling and further stirred. After completion of the reaction, chloroform was added thereto and the resulting organic layer was washed with a 5% citric acid solution, a saturated sodium bicarbonate solution and water in this order, dried over anhydrous sodium sulfate and then filtered. The solvent was removed by evaporation, and the resulting residue was purified by silica gel column chromatography (ethyl acetate) to obtain the objective compound as a colorless oily material as one of its diastereomer (15.4 mg), as well as the other diastereomer (16.9 mg).

1. customThe compound obtained (99.2 mg, 0.42 mmol)
2. additionwas added
3. washthe resulting organic layer was washed with a 5% citric acid solution
4. dry with materiala saturated sodium bicarbonate solution and water in this order, dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customThe solvent was removed by evaporation
7. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate)
8. customto obtain the objective compound as a colorless oily material as one of its diastereomer (15.4 mg)

ORD-Eintrag

ord-da5e4b54ff364296a41d30b063dbbb2d

Quelldatensatz

uspto-grants-1999_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05907039