Ethyl 1-[(R)-1-Phenylethyl]hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate → Ethyl hexahydropyrrolo[3,4-B]pyrrole-5(1H)-carboxylate

HRID 912482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 912482
C1([C@H]([N:9]2[CH:13]3[CH2:14][N:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH:12]3[CH2:11][CH2:10]2)C)C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH:9]1[CH2:10][CH2:11][CH:12]2[CH2:16][N:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH:13]12

Komponenten

4

Edukt 1

HCID 66758144Ethyl 1-[(R)-1-Phenylethyl]hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate2×

Produkt 1

HCID 19100952Ethyl hexahydropyrrolo[3,4-B]pyrrole-5(1H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

5% palladium hydroxide on activated carbon (13.9 g, 50% w/w in water) was added to a pressure reactor. The product of Example A3 (as 506.8 g of a 25.9 wt % solution of ethyl 1-((R)-1-phenylethyl)hexahydropyrrolo[2,3-c]pyrrole-5(1H)-carboxylate (131.3 g) in MeOH was added, followed by a MeOH rinse (37 g). The mixture was heated to 50° C. under an atmosphere of hydrogen (40 psi) for 4 hours. The mixture was filtered through HYFLO Filter Aid (HYFLO is a registered trademark of Celite Products Company of Los Angeles, Calif.) and rinsed with 200 mL of MeOH to provide a solution containing 78.9 g of the title compound.

Aufarbeitung

  1. washrinse (37 g)
  2. filtrationThe mixture was filtered through HYFLO
  3. filtrationFilter Aid (HYFLO
  4. wash) and rinsed with 200 mL of MeOH
  5. customto provide a solution

Quellen und Nachweise

ORD-Eintrag
ord-69b989b0f3ba442aa7dc339b3fea448c
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026240B2

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