N-benzyl-N-methyl-1-phenylmethanamine → 3-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-propionic acid tert-butyl ester

HRID 491908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491908
[CH2:1]([N:8](C)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([Li])CCC.[C:22]([O:26][C:27](=[O:36])[CH:28]=[CH:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)([CH3:25])([CH3:24])[CH3:23]>C1COCC1>[C:22]([O:26][C:27](=[O:36])[CH2:28][CH:29]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:17])[CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1)([CH3:25])([CH3:23])[CH3:24]

Komponenten

5

Edukt 3

HCID 21583N-benzyl-N-methyl-1-phenylmethanamineHCID 544765093-Cyclohexyl-acrylic acid tert-butyl esterHCID 178418339Butyllithium

Produkt 1

HCID 670236593-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-propionic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of N-benzyl-(+)-methyl-benzylamine (8.5 mL, 40.4 mmol) in THF (100 mL) was cooled to 0° C., then n-butyl lithium (16 mL, [2.5 M], 40.4 mmol) was added and the resulting mixture stirred for 1 hour. The reaction mixture was cooled to −78° C., then a solution of 3-cyclohexyl-acrylic acid tert-butyl ester (7.71 g, 36.7 mmol) in THF (20 mL) was added dropwise for 30 min and the resulting mixture was stirred an additional 1 hour at −78° C. The reaction was quenched with NH4CT (s), and extracted with EtOAc, the organic layer was dried with MgSO4, filtered and evaporated under reduced pressure to yield a residue. The residue was purified by column chromatography (10%-70% EtOAc/heptane) to yield a residue.

Aufarbeitung

  1. stirringthe resulting mixture was stirred an additional 1 hour at −78° C
  2. customThe reaction was quenched with NH4CT (s)
  3. extractionextracted with EtOAc
  4. dry with materialthe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto yield a residue
  8. customThe residue was purified by column chromatography (10%-70% EtOAc/heptane)
  9. customto yield a residue

Quellen und Nachweise

ORD-Eintrag
ord-8782923e3a4648ad96a38f66f191daf4
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531545B2

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