Triethylamine → 4-(2-Hydroxy-ethoxy)-phenyl-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

HRID 552582

Reaktionsgleichung

Reaktionsgleichung von HRID 552582
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>ClCCl>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:11])=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 2724699PyBOPHCID 43122544-(2-Hydroxyethoxy)benzenecarboxylic acid

Produkt 1

HCID 119604194-(2-Hydroxy-ethoxy)-phenyl-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanoneAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-(2-Hydroxy-ethoxy)-benzoic acid (152 mg, 0.84 mmol), (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (193 mg, 1.25 mmol) and triethylamine (303 mg, 3.0 mmol) are dissolved in dichloromethane (5.0 mL) and benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP) (786 mg, 1.5 mmol) is added to the mixture. The mixture is stirred at room temperature for 3 days. The reaction mixture is diluted with dichloromethane, washed with brine, dried over Na2SO4, filtered and evaporated. The crude product is purified using silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH=20:1) to give 177 mg (66%) of the title compound. Observed Mass 319.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product is purified

Quellen und Nachweise

ORD-Eintrag
ord-6607de3a9eb3496199ab018dd70bd4ee
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951826B2

Verknüpfte Notizen

Wird geladen…