2-(Di-tert-butylphosphino)biphenyl → (S)-1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine

HRID 40507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40507
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH:9]2[CH2:12][NH:11][CH2:10]2)=[CH:6][CH:5]=1)[CH3:2].C(OC(=O)[NH:21][C@H:22]([C:24]1[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=1)[CH3:23])(C)(C)C.CC([O-])(C)C.[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1.O.CO>[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH:9]2[CH2:12][N:11]([C:27]3[CH:28]=[CH:29][C:24]([C@@H:22]([NH2:21])[CH3:23])=[CH:25][CH:26]=3)[CH2:10]2)=[CH:6][CH:5]=1)[CH3:2]

Komponenten

8

Edukt 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23665647Potassium tert-butoxideHCID 534093113-(4-Ethoxyphenoxy)azetidineHCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate

Produkt 1

HCID 86689010(S)-1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To 5.0 g (21.8 mmol) 3-(4-ethoxy-phenoxy)-azetidine and 6.5 g (21.8 mmol) (S)-[1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (1.3) in 80 mL 1,4-dioxane under an argon atmosphere are added 8.6 g (87.1 mmol) KOtBu, 0.65 g (2.18 mmol) 2-(di-tert-butylphosphino)biphenyl and 1.0 g (1.09 mmol) tris-(dibenzylideneacetone)-dipalladium(0). The mixture is stirred for 2 h at 120° C. Subsequently 200 mL MeOH and 5 mL water are added and the mixture is filtered and concentrated in vacuo. The residue is taken up in ethyl acetate and is washed with water. The organic layer is concentrated and the residue is purified by HPLC (eluent A: water+0.1% NH4OH, eluent B: MeOH) to yield the desired product.

Aufarbeitung

  1. filtrationthe mixture is filtered
  2. concentrationconcentrated in vacuo
  3. washis washed with water
  4. concentrationThe organic layer is concentrated
  5. customthe residue is purified by HPLC (eluent A: water+0.1% NH4OH, eluent B: MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-fdb4a14c01f14561a6767d063c044631
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530461B2

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