tert-Butyl 3-bromopropionate → tert-Butyl 3-[(3-cyanobenzyl)(methyl)amino]propanoate

HRID 219883

Reaktionsgleichung

Reaktionsgleichung von HRID 219883
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].C(=O)(O)[O-].[Na+].[C:17]([O:21][C:22](=[O:26])[CH2:23][CH2:24]Br)([CH3:20])([CH3:19])[CH3:18]>C(#N)C>[C:7]([C:6]1[CH:5]=[C:4]([CH:11]=[CH:10][CH:9]=1)[CH2:3][N:2]([CH3:1])[CH2:24][CH2:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:26])#[N:8]

Komponenten

5

Edukt 3

HCID 256128tert-Butyl 3-bromopropionateHCID 4575953-(Methylaminomethyl)benzonitrileHCID 516892Sodium Bicarbonate

Produkt 1

HCID 66678103tert-Butyl 3-[(3-cyanobenzyl)(methyl)amino]propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-[(methylamino)methyl]benzonitrile (6.1 g, 0.0417 mol) and sodium bicarbonate (7 g, 0.0834 mol) in acetonitrile (70 mL) under N2, was added tert-butyl-3-bromo-propanoate (7 mL, 0.0417 mol) in dropwise. After being stirred at RT for 12 h, the reaction mixture was filtered and the filterate was concentrated under reduced pressure. The obtained crude was purified using column chromatography on neutral silica gel (pet ether/EtOAc) to afford the title compound as a pale yellow liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.69-7.70 (s, 2H), 7.59-7.61 (m, 1H), 7.49-7.53 (m, 1H), 3.49 (s, 2H), 2.56-2.59 (m, 2H), 2.34-2.38 (m, 2H), 2.09 (s, 3H), 1.38 (s, 9H).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filterate was concentrated under reduced pressure
  3. customThe obtained crude
  4. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-557cfc614035461eb285200d40656b02
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

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