Potassium Carbonate → (2S,5R)-4-[3-(6-bromo-chroman-3-ylamino)-propyl]-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 1986632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986632
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH:6]([NH2:12])[CH2:5]2.[C:13]([O:17][C:18]([N:20]1[CH2:25][C@@H:24]([CH3:26])[N:23]([CH2:27][CH2:28][CH2:29]Cl)[CH2:22][C@@H:21]1[CH3:31])=[O:19])([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:25][C@@H:24]([CH3:26])[N:23]([CH2:27][CH2:28][CH2:29][NH:12][CH:6]2[CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[O:8][CH2:7]2)[CH2:22][C@@H:21]1[CH3:31])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 162444326-Bromochroman-3-amineHCID 57722505(2S,5R)-4-(3-chloro-propyl)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 68866043(2S,5R)-4-[3-(6-bromo-chroman-3-ylamino)-propyl]-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl esterAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 6-bromo-chroman-3-ylamine (0.105 g, 0.46 mmol, 1 eq), (2S,5R)-4-(3-chloro-propyl)-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (0.133 g, 0.46 mmol, 1 eq), K2CO3 (0.127 g, 0.92 mmol, 2 eq), and Kl (0.017 g, 0.10 mmol, 0.2 eq) in DMF (0.5 mL) was heated in a microwave reactor at 150° C. for 25 min. The reaction mixture was partitioned between EtOAc (3 mL) and 10% aqueous NaHCO3 (3 mL). The organic layer was separated and aqueous layer was extracted with EtOAc (2 mL×3). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give 0.22 g (100%) of (2S,5R)-4-[3-(6-bromo-chroman-3-ylamino)-propyl]-2,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester as a yellow oil. The material was carried on to next step without further purification.

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc (3 mL) and 10% aqueous NaHCO3 (3 mL)
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted with EtOAc (2 mL×3)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6690ffd8115142f48e3a709399f8d63c
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550467B2

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