Diisopropylethylamine → rac-N-(3-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2,N-dimethyl-propionamide

HRID 220318

Reaktionsgleichung

Reaktionsgleichung von HRID 220318
[CH3:1][O:2][CH2:3][C:4]([CH2:9][O:10][CH3:11])([CH3:8])[C:5]([OH:7])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:45][N:46]([CH2:64][CH2:65][CH2:66][NH:67][CH3:68])[CH2:47][CH2:48][C:49]1([OH:63])[CH2:54][CH:53]2[CH2:55][CH2:56][CH:50]1[CH:51]=[C:52]2[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>C(Cl)Cl>[OH:63][C@@:49]1([CH2:48][CH2:47][N:46]([CH3:45])[CH2:64][CH2:65][CH2:66][N:67]([CH3:68])[C:5](=[O:7])[C:4]([CH2:3][O:2][CH3:1])([CH3:8])[CH2:9][O:10][CH3:11])[CH2:54][C@H:53]2[CH2:55][CH2:56][C@@H:50]1[CH:51]=[C:52]2[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 219119313-Methoxy-2-(methoxymethyl)-2-methylpropanoic acidHCID 68413377rac-(1R*,2R*,4R*)-2-{2-[methyl-(3-methylamino-propyl)-amino]-ethyl}-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

Produkt 1

HCID 68413389rac-N-(3-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2,N-dimethyl-propionamideAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 65 mg 3-methoxy-2-methoxymethyl-2-methyl-propionic acid in 0.5 mL DCM was added 0.14 mL DIPEA followed by 133 mg HATU. The resulting mixture was stirred at rt for 20 min before 88 mg of rac-(1R*,2R*,4R*)-2-{2-[methyl-(3-methylamino-propyl)-amino]-ethyl}-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol, dissolved in 1 mL DCM was added. After stirring overnight the reaction was quenched with water. The water phase was extracted with DCM, the combined organic phases were washed with brine, dried and concentrated in vacuo. The residue was purified by CC with EtOAc-MeOH (3:1) to obtain 115 mg of rac-N-(3-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2,N-dimethyl-propionamide as colorless oil.

Aufarbeitung

  1. additionwas added
  2. customwas quenched with water
  3. extractionThe water phase was extracted with DCM
  4. washthe combined organic phases were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by CC with EtOAc-MeOH (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-93485bb4680b41159d26694fe08bc57a
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202885B2

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