4-Methylmorpholine → (2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidine

HRID 1720532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720532
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]([OH:24])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)=[O:7])(C)(C)C.[C:25]([O:29][C:30]([N:32]1[CH2:39][CH2:38][CH2:37][C@H:33]1C(O)=O)=[O:31])([CH3:28])([CH3:27])[CH3:26].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>Cl.O1CCOCC1>[C:25]([O:29][C:30]([N:32]1[CH2:39][CH2:38][CH2:37][C@H:33]1[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]([OH:24])[CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)=[O:7])=[O:31])([CH3:28])([CH3:26])[CH3:27]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 57133844(S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-2-(p-methoxyphenoxy)ethyl]pyrrolidine

Produkt 1

HCID 22860058(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidineAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 204431481,4-Dioxane hydrochlorideLösungsmittel

Versuchsvorschrift

(2S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-2-(4-methoxyphenoxy)ethyl]pyrrolidine (1.57 g) was dissolved in 4N hydrochloric acid/1,4-dioxane (23 ml), and the mixture was stirred at room temperature for 1 hour. The residue obtained by concentration and drying of the reaction mixture was dissolved in DMF (15 ml), and subjected to the condensation reaction using N-(tert-butoxycarbonyl)-L-proline (1.00 g), N-methylmorpholine (0.51 ml), HOBt (0.75 g) and DCC (0.96 g) in the same manner as in Example 46-C) to give 1.41 g of the title compound.

Aufarbeitung

  1. customThe residue obtained by concentration
  2. customdrying of the reaction mixture
  3. dissolutionwas dissolved in DMF (15 ml)
  4. customsubjected to the condensation reaction

Quellen und Nachweise

ORD-Eintrag
ord-0e3d9cd70a134f2a88951f925dc56bff
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506256

Notizen zur Reaktion

Wird geladen…