Diisopropylethylamine → 1,1-Dimethylethyl (2S)-4-[(2-chloro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 534782

Reaktionsgleichung

Reaktionsgleichung von HRID 534782
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[Cl:12].Cl.[CH3:14][C@H:15]1[CH2:20][NH:19][CH2:18][CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[CH2:2][N:19]1[CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:15]([CH3:14])[CH2:20]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 30163681-(Bromomethyl)-2-chloro-4-nitrobenzeneHCID 45072182(S)-tert-butyl 2-methylpiperazine-1-carboxylate hydrochloride

Produkt 1

HCID 592621281,1-Dimethylethyl (2S)-4-[(2-chloro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylateAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of crude 1-(bromomethyl)-2-chloro-4-nitrobenzene (D102) (0.391 g), 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate hydrochloride (0.407 g, 1.72 mmol) and Hunig's base (0.625 mL, 3.59 mmol) in dry DMF (3 mL) was stirred at room temperature for 10 minutes. The reaction mixture was concentrated to give an orange oil which was dissolved in DCM and washed with water (×2) and brine, then dried and concentrated to give an orange oil. Purification by column chromatography eluting with 0-30% EtOAc/pentane gave the title compound as a yellow oil (0.199 g). δH (CDCl3, 400 MHz) 8.24 (1H, d), 8.12 (1H, dd), 7.77 (1H, d), 4.24 (1H, br.s), 3.85 (1H, d), 3.63 (2H, s), 3.14 (1H, td), 2.76 (1H, m), 2.59 (1H, m), 2.33 (1H, dd), 2.18 (1H, m), 1.47 (9H, s), 1.28 (3H, d). MS (ES): MH+ 370/372,

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto give an orange oil which
  3. washwashed with water (×2) and brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an orange oil
  7. customPurification by column chromatography
  8. washeluting with 0-30% EtOAc/pentane

Quellen und Nachweise

ORD-Eintrag
ord-92ef30901bb549da81580cf8c3595c75
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853218B2

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