Reaktion #64895

ord-4e02f4b9987040908d5e8a1e8c051415

Reaktionsgleichung

CC1(C)Oc2ccc([N+](=O)[O-])cc2[C@@H](N2CCCC2=O)[C@@H]1O
trans-3,4-dihydro-2,2-dimethyl-6-nitro-4-(2-oxopyrrolidin-1-yl)-2H-1-benzopyran-3-ol
→
CC1(C)Oc2ccc(N)cc2[C@@H](N2CCCC2=O)[C@@H]1O
title compound
CC1(C)Oc2ccc(N)cc2[C@@H](N2CCCC2=O)[C@@H]1O
TRANS-6-AMINO-3,4-DIHYDRO-2,2-DIMETHYL-4-(2-OXOPYRROLIDIN-1-YL)-2H-1 -BENZOPYRAN-3-OL

Edukte

CC1(C)Oc2ccc([N+](=O)[O-])cc2[C@@H](N2CCCC2=O)[C@@H]1O
trans-3,4-dihydro-2,2-dimethyl-6-nitro-4-(2-oxopyrrolidin-1-yl)-2H-1-benzopyran-3-ol

Reagenzien

[Pd]
Pd/C

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe reaction mixture is filtered
  2. 2
    Sonstigeevaporated
  3. 3
    Sonstigeevaporated

Vorschrift

To a solution of 8.0 g (0.025 mol) of trans-3,4-dihydro-2,2-dimethyl-6-nitro-4-(2-oxopyrrolidin-1-yl)-2H-1-benzopyran-3-ol (U.S. Pat. No. 4,647,670) in 800 mL of ethanol is added 2.8 g of 10% Pd/C, and the reaction mixture is stirred under a hydrogen atmosphere for 18 h. The reaction mixture is filtered, evaporated, and the resulting oil subjected to chromatography on silica gel utilizing 4% methanol in dichloromethane as eluent. The eluates are analyzed by thin layer chromatography, and the appropriate fractions are combined and evaporated to afford the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05416097uspto-grants-1995_05