Hydrochloric Acid → 4-Cyclohexyl-l-proline

HRID 1732120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1732120
C(OC([N:11]1[CH2:15][C@H:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:13][C@H:12]1[CH2:22][OH:23])=O)C1C=CC=CC=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:25].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.Cl>CN(C)C=O>[CH:16]1([CH:14]2[CH2:15][NH:11][C@H:12]([C:22]([OH:23])=[O:25])[CH2:13]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 2724130Cornforth reagentHCID 13648262(2S-trans)-1-[(Benzyloxy)carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol

Produkt 1

HCID 186648034-Cyclohexyl-l-proline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (2S-trans)-1-[(benzyloxy)-carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol (0.65 g) in dimethylformamide (10 ml) was added pyridinium dichromate (2.1 g). The mixture was stirred at room temperature for 16 hours and poured onto crushed ice and hydrochloric acid (25 ml). Extraction with ethyl acetate followed by solvent evaporation yielded 0.4 g of (trans)-1-[benzyloxy)carbonyl]-4-cyclohexyl-L-proline as a thick oil. The compound can be deprotected using catalytic hydrogenation as described in Method V.

Aufarbeitung

  1. additionpoured
  2. extractionExtraction with ethyl acetate
  3. customfollowed by solvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a0793f0a994847b792f8353a874b7733
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04625038

Notizen zur Reaktion

Wird geladen…