Potassium Carbonate → 4-[(4-Cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester

HRID 1814643

Reaktionsgleichung

Reaktionsgleichung von HRID 1814643
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:20]1(=[C:23]2[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]2)[CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCC(Cl)C.ClCCl.C(O)(=O)C>[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH:26]2[CH2:27][CH2:28][C:23](=[C:20]3[CH2:22][CH2:21]3)[CH2:24][CH2:25]2)=[CH:7][CH:6]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 225021744-Cyclopropylidenecyclohexanone

Produkt 1

HCID 235501404-[(4-Cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl esterAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 65641,2-DichloropropaneLösungsmittel

Versuchsvorschrift

4-Aminomethylbenzoic acid methyl ester, hydrochloride salt (2.2 g, 11 mmol) was suspended in 1,2 dichloropropane (30 mL) and an aqueous saturated solution of potassium carbonate (15 mL) was added. The next day the organic phase was isolated and dried (MgSO4). 4-Cyclopropylidenecyclohexanone (1.5 g, 11 mmol) dissolved in dichloromethane (15 mL) was added followed by addition of acetic acid (400 μL) and sodium triacetoxyborohydride (3.3 g, 16.5 mmol). After 72 hours at 20° C. the reaction mixture was diluted with dichloromethane (50 mL) and washed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (50 g silica) using ethyl acetate and methanol (97:3) as eluent to give 1.1 g of 4-[(4-cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester.

Aufarbeitung

  1. customThe next day the organic phase was isolated
  2. dry with materialdried (MgSO4)
  3. additionwas added
  4. washwashed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (50 g silica)

Quellen und Nachweise

ORD-Eintrag
ord-c4ba3e59128141eda86fbc76a7a03416
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875760B2

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