4-Methylmorpholine → N-[[1-[(2,5-dimethylphenyl)acetyl]-4-piperidinyl]carbonyl]-DL-serine methyl ester

A mixture of 1-[(2,5-dimethylphenyl)acetyl]-4-piperidinecarboxylic acid (i.e. the product of Example 9, Step B) (1.44 g, 5.23 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.1 g, 5.75 mmol), and N-methylmorpholine (529 mg, 5.23 mmol) in 5 mL of dichloromethane was stirred at room temperature for 15 minutes. DL-Serine methyl ester hydrochloride (814 mg, 5.23 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction was partitioned between 1 N aqueous hydrochloric acid (10 mL) and dichloromethane (10 mL), and the organic layer was washed with 1 N aqueous hydrochloric acid, water and brine, dried over MgSO4 and concentrated under reduced pressure to give 1.61 g of the title compound.

1. stirringthe reaction mixture was stirred at room temperature for 16 h
2. customThe reaction was partitioned between 1 N aqueous hydrochloric acid (10 mL) and dichloromethane (10 mL)
3. washthe organic layer was washed with 1 N aqueous hydrochloric acid, water and brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-c1957aede7c14c9abba05e8f32af8d25

Quelldatensatz

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08586611B2