Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate

HRID 1044048

Reaktionsgleichung

Reaktionsgleichung von HRID 1044048
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[C:17]1([CH:23]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[C:24]([OH:26])=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[C:17]1([CH:23]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[C:24]([O:26][C@@H:47]2[CH:48]3[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]3)[CH2:46]2)=[O:25])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67124826Phenyl-o-methylphenylamino-acetic acid hydrochloride

Produkt 1

HCID 46840573(R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetateAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

PS-DCC (1.15 g, 1.44 mmol, loading: 1.25 mmol/g) was suspended in THF (15 ml). 2-Phenyl-2-(o-tolylamino)acetic acid hydrochloride (I22) (200 mg, 0.72 mmol) and HOBT (221 mg, 1.44 mmol) were added, followed by (R)-quinuclidin-3-ol (275 mg, 2.16 mmol), and the mixture was stirred for 16 hours at room temperature. PS-DCC was removed by filtration, and the filtrate was evaporated. The resulting residue was dissolved in EtOAc and washed sequentially with water, sat. NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give the title compound (260 mg, quantitative yield, mixture of diastereomers).

Aufarbeitung

  1. customPS-DCC was removed by filtration
  2. customthe filtrate was evaporated
  3. dissolutionThe resulting residue was dissolved in EtOAc
  4. washwashed sequentially with water, sat. NaHCO3, water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d70e26e257bd4bc6922ebf2e9eb74833
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563577B2

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