Benzaldehyde → 4-Benzylamino-cyclohexanecarboxylic acid methyl ester

HRID 444715

Reaktionsgleichung

Reaktionsgleichung von HRID 444715
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8][CH2:7]1)=[O:5].[O-]S([O-])(=O)=O.[Mg+2].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+]>CO.O>[CH3:2][O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][CH2:7]1)=[O:5]

Komponenten

7

Edukt 4

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 178501210HCID 178501210, Verbindung

Produkt 1

HCID 216279964-Benzylamino-cyclohexanecarboxylic acid methyl esterAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of trans-4-amino-cyclohexylcarboxylic acid methyl ester hydrochloride (4.5 g, 23.24 mmol) in MeOH (30 mL) is added TEA (1.3 mL, 9.339 mmol), MgSO4 (4.2 g, 34.88 mmol), and benzaldehyde (2.5 mL, 24.74 mmol). The mixture stirs 1 h. The mixture is then cooled to 0° C. and NaBH4 (5.0 g, 132.2 mmol) is added portionwise over 0.5 h. The mixture stirs 1 h at ambient temperature. Then H2O (200 mL) is added and the mixture is extracted with EtOAc (2×500 mL), dried and concentrated. The resulting solid is purified by flash chromatography (gradient elution: 0-100% EtOAc/Hep) which affords 2.7 g of 4-benzylamino-cyclohexanecarboxylic acid methyl ester. LC/MS: [M+H]+ 248, Rt=0.82 min (method 11).

Aufarbeitung

  1. waitThe mixture stirs 1 h at ambient temperature
  2. extractionthe mixture is extracted with EtOAc (2×500 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting solid is purified by flash chromatography (gradient elution: 0-100% EtOAc/Hep) which

Quellen und Nachweise

ORD-Eintrag
ord-b38515c7b60840769501d950406c8163
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476224B2

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