Reaktion #506496

Reaktionsgleichung

Phenylmethyl 4-[(3-methyl-4-nitrophenyl)oxy]-1-piperidinecarboxylate

Sodium borohydride

sodium borohydride

→

title compound

Ausbeute 78.0%

phenylmethyl 4-[(4-amino-3-methylphenyl)oxy]-1-piperidinecarboxylate

Ausbeute 78.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 20 min
2. 2
   workup.STIRRINGthe mixture was stirred for 10 min more
3. 3
   SonstigeThe reaction was quenched by the addition of approximately 15 mL of 2N sodium hydroxide solution
4. 4
   workup.ADDITIONThe mixture was poured into EtOAc and H2O
5. 5
   Sonstigethe layers were separated
6. 6
   WaschenThe organic layer was washed with brine
7. 7
   Extraktionthe combined aqueous layers were extracted with EtOAc
8. 8
   TrocknenThe combined organic layers were dried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated in vacuo
11. 11
    SonstigeThe residue was purified by flash chromatography

Vorschrift

Phenylmethyl 4-[(3-methyl-4-nitrophenyl)oxy]-1-piperidinecarboxylate (0.798 g, 2.15 mmol) was dissolved in 20 mL of MeOH with stirring. Nickel(II) chloride hexahydrate (0.256 g, 1.08 mmol) was added and the mixture was cooled to 0° C. Sodium borohydride (0.163 g, 4.31 mmol) was added, and the mixture was stirred for 20 min. Additional sodium borohydride (˜20 to 30 mg) was added, and the mixture was stirred for 10 min more. The reaction was quenched by the addition of approximately 15 mL of 2N sodium hydroxide solution. The mixture was poured into EtOAc and H2O, and the layers were separated. The organic layer was washed with brine, and the combined aqueous layers were extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford 0.568 g (78%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.40-7.23 (m, 5H), 6.61-6.43 (m, 3H), 5.04 (s, 2H), 4.37 (s, 2H), 4.27-4.17 (m, 1H), 3.74-3.57 (m, 2H), 3.27-3.12 (m, 2H), 1.97 (s, 3H), 1.86-1.73 (m, 2H), 1.52-1.39 (m, 2H).

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