Reaktion #1135657

Reaktionsgleichung

sodium triacetoxyborohydride

2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxo-1-((S)-1-oxobutan-2-yl)piperidin-3-yl)acetic acid

3,3-dimethylmorpholine hydrochloride

→

title compound

2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(3,3-dimethylmorpholino)butan-2-yl)-3-methyl-2-oxopiperidin-3-yl)acetic acid

Lösungsmittel

NH4Cl

DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with DCM (2×)
2. 2
   WaschenThe combined organic layers were washed with sat. aq. NaCl solution
3. 3
   Trocknendried over anhydrous Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenthe filtrate was concentrated
6. 6
   SonstigeThe residue was purified by preparative thin layer chromatography on silica gel (eluent: 50% ethyl acetate/hexanes)
7. 7
   workup.ADDITIONThe product containing fractions
8. 8
   Einengenconcentrated
9. 9
   Sonstigerepurified by preparative thin layer chromatography on silica gel (eluent: 10% MeOH/DCM)

Vorschrift

To a solution of 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxo-1-((S)-1-oxobutan-2-yl)piperidin-3-yl)acetic acid (70 mg, 0.151 mmol; Example 210, Step A) in DCE (3 mL) was added 45.9 mg (0.303 mmol) of 3,3-dimethylmorpholine hydrochloride (Cottle, D.; Jeltsch, A.; Stoudt, T.; Walters, D. Journal of Organic Chemistry. 1946, 11(3), 286-91.; Note: reference is for the free base) and sodium triacetoxyborohydride (64.2 mg, 0.303 mmol). After stirring overnight, the mixture was diluted with sat. aq. NH4Cl solution. The mixture was extracted with DCM (2×). The combined organic layers were washed with sat. aq. NaCl solution, dried over anhydrous Na2SO4, filtered and the filtrate was concentrated. The residue was purified by preparative thin layer chromatography on silica gel (eluent: 50% ethyl acetate/hexanes). The product containing fractions were pooled, concentrated and repurified by preparative thin layer chromatography on silica gel (eluent: 10% MeOH/DCM) to afford the title compound.

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