Benzylamine → HCID 25223591, Verbindung

HRID 533185

Reaktionsgleichung

Reaktionsgleichung von HRID 533185
CS(O[CH2:6][C@@H:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8]1)(=O)=O.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCOC(C)=O.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>CC#N.[O-][Mo]([O-])(=O)=O>[CH2:14]([NH:21][CH2:6][C@@H:7]1[CH2:11][O:10][C:9]([CH3:12])([CH3:13])[O:8]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

7

Edukt 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 10236NinhydrinHCID 24903512[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate

Produkt 1

HCID 25223591HCID 25223591, VerbindungAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24621Molybdate ionKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The title compound was prepared in the same way as that method described for preparing the (S)-enantiomer (M. Lemaire, F. Posada, J.-G. Gourcy and G. Jeminet, Synlett, 1995, 627). A solution of (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (3.0 g, 14.27 mmol) and benzylamine (6.23 ml, 57.1 mmol) were refluxed together in CH3CN (38 ml) for 48 h. Tlc (EtOAc-hex 8:2) showed a new product (uv/molybdate or ninhydrin) with Rf ˜0.3 together with a little higher running sm. The solvent was evaporated and the residue dissolved in EtOAc and washed with aqueous sat. NaHCO3, dried and the solvent evaporated. The residue was chromatographed (EtOAc-hex, 6:4 then 8:2) to give (R)—N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine (2.56 g, 11.57 mmol, 81% yield) as a yellow oil. [α]D21 −3.7 (c, 0.885, CHCl3). 1H NMR (CDCl3, 300 MHz), δ ppm, 7.32-7.20 (m, 5H), 4.25, (m, 1H), 4.03 (dd, 1H, J 8.0, 6.4 Hz), 3.82 (s, 2H), 3.68 (dd, 1H, J 8.0, 6.8 Hz), 2.74 (d, 2H, J 5.7 Hz), 1.40 (s, 3H), 1.35 (s, 3H). 13C NMR (CDCl3, 75.5 MHz), δ ppm, 140.6, 128.8, 128.4, 127.3, 109.5, 75.8, 67.9, 54.4, 52.1, 27.3, 25.8.

Aufarbeitung

  1. customThe title compound was prepared in the same way as that method
  2. customdescribed for preparing the (S)-enantiomer (M. Lemaire, F. Posada, J.-G. Gourcy and G. Jeminet, Synlett, 1995, 627)
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with aqueous sat. NaHCO3
  6. customdried
  7. customthe solvent evaporated
  8. customThe residue was chromatographed (EtOAc-hex, 6:4

Quellen und Nachweise

ORD-Eintrag
ord-b5504589053e4655a73fe4a91c83c464
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853224B2

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