Methanol → N-[(3R)-1-Azabicyclo[2.2.2]Oct-3-yl]4-Phenoxybenzamide

HRID 2297645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2297645
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OP(Cl)(OC2C=CC=CC=2)=O)C=CC=CC=1.[NH2:34][C@@H:35]1[CH:40]2[CH2:41][CH2:42][N:37]([CH2:38][CH2:39]2)[CH2:36]1.CO>C(Cl)Cl>[N:37]12[CH2:42][CH2:41][CH:40]([CH2:39][CH2:38]1)[C@@H:35]([NH:34][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=1)[CH2:36]2

Komponenten

6

Edukt 4

HCID 887MethanolHCID 751824-Phenoxybenzoic acidHCID 75654Diphenyl chlorophosphateHCID 719215(3R)-1-Azabicyclo(2.2.2)octan-3-amine

Produkt 1

HCID 7831595N-[(3R)-1-Azabicyclo[2.2.2]Oct-3-yl]4-PhenoxybenzamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TEA (50 μL, 0.35 mmol) is added to a suspension of 4-phenoxybenzoic acid (75 mg, 0.35 mmol) in CH2Cl2 (1 mL). Diphenylchlorophosphate (62, μL, 0.3 mmol) is added and the resulting solution is stirred at room temperature for 30 minutes. A solution of (R)-3-aminoquinuclidine (IM in DMF, 0.2 mL, 0.2 mmol) is added and the resulting solution is stirred overnight at room temperature. MeOH is added and the mixture is poured through a column of AG50 W ×2 ion exchange resin (H+form). The resin is washed with MeOH and then the product is eluted with 5% TEA in MeOH. The eluent is evaporated to dryness to yield the desired product (49 mg, 76%). MS for C2GH22N2O2 (ESI) (M+H)+ m/z 323.

Aufarbeitung

  1. stirringthe resulting solution is stirred overnight at room temperature
  2. additionthe mixture is poured through a column of AG50 W ×2 ion exchange resin (H+form)
  3. washThe resin is washed with MeOH
  4. washthe product is eluted with 5% TEA in MeOH
  5. customThe eluent is evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4fb776e5310a455abb72999bf2aad25b
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06492386B2

Notizen zur Reaktion

Wird geladen…