Reaktion #160364

Reaktionsgleichung

3-[(4-Methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

sodium borohydride

→

3-[(trans-4-Hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

Ausbeute 62.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with a 10% solution of hydrochloric acid (5 ml)
2. 2
   Extraktionthe aqueous phase was extracted with ethyl acetate (3×10 mL)
3. 3
   TrocknenThe combined ethyl acetate layer was dried (Na2SO4)
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was then purified by preparative chromatography (3% MeOH/CH2Cl2)

Vorschrift

3-[(4-Methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (55 mg, 0.121 mmol) was dissolved in methanol (1.2 ml), cooled to 0° C. and then sodium borohydride (4.6 mg, 0.121 mmol) was added. After 30 minutes of stirring at 0° C., the reaction was quenched with a 10% solution of hydrochloric acid (5 ml) and the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined ethyl acetate layer was dried (Na2SO4) and concentrated. The residue was then purified by preparative chromatography (3% MeOH/CH2Cl2) to obtain 34 mg (62%) of 3-[(trans-4-Hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester.

Quelle