4-[(2R)-3-Amino-2-hydroxyprop-1-yl]morpholine → (S)-5-[3-(2-hydroxy-3-morpholin-4-yl-propylamino)-propyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

Participants

Reaction Conditions

Reaction Steps

5-(3-methanesulfonyloxy-propyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1 g (1.13 g, 2.9 mmol) was dissolved in 5.6 ml of dichloromethane under stirring, and added with (R)-1-amino-3-morpholin-4-yl-propan-2-ol 78c (0.93 g, 5.8 mmol) to the solution at room temperature. Upon the completion of the addition, the reaction mixture was heated to 45° C. for 14 hours in an oil bath. After thin lay chromatography showed the disappearance of starting materials, the reaction was stopped. The reaction solution was added with 15 ml of saturated brine, extracted with dichloromethane (20 ml×3), the combined organic phase was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the title compound (S)-5-[3-(2-hydroxy-3-morpholin-4-yl-propylamino)-propyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 78d (600 mg, yield 72.5%) as a yellow oil.

Provenance & Evidence