Benzyl Bromide → (E)-3-{1'-benzyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester

HRID 518168

Reaktionsgleichung

Reaktionsgleichung von HRID 518168
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][N:14]([C:17](OC(C)(C)C)=O)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:28].C(Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][N:14]([CH2:17][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:28]

Komponenten

4

Edukt 2

HCID 7498Benzyl BromideHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester2×

Produkt 1

HCID 52952515(E)-3-{1'-benzyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl esterAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of (E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (451 mg, 1.34 mmol, Intermediate 1) in DCM (12 ml) was treated with TEA (0.42 ml, 3 mmol) and benzyl bromide (0.54 ml, 4.5 mmol), and stirred at RT for 5 h. The mixture was washed with water, the pH value was adjusted to 5 with a 0.5 M HCl, then dried and concentrated. The crude residue was purified by column chromatography (eluent: DCM/MeOH 95:5) to give (E)-3-{1′-benzyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (440 mg) as a light yellow solid.

Aufarbeitung

  1. washThe mixture was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe crude residue was purified by column chromatography (eluent: DCM/MeOH 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-1893f216414a4acb90db61104d58587e
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115148B2

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