2,4-Dimethoxybenzyl alcohol → rac-(trans)-Cyclopentane-1,2-dicarboxylic acid mono-(2,4-dimethoxy-benzyl)ester

HRID 547849

Reaktionsgleichung

Reaktionsgleichung von HRID 547849
[C@@H:1]1([C:9]([OH:11])=[O:10])[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([OH:8])=[O:7].[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16]O.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C.O.C([O-])(O)=O.[Na+]>[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][O:7][C:6]([C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:1]1[C:9]([OH:11])=[O:10])=[O:8]

Komponenten

8

Edukt 3

HCID 817502,4-Dimethoxybenzyl alcoholHCID 7273751,2-Cyclopentanedicarboxylic acid, (1R,2R)-rel-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 67153742rac-(trans)-Cyclopentane-1,2-dicarboxylic acid mono-(2,4-dimethoxy-benzyl)ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of (trans)-cyclopentane-1,2-dicarboxylic acid (1.90 g, 12 mmol), 2,4-dimethoxy-benzyl alcohol (2.02 g, 12 mmol), DMAP (73 mg, 0.6 mmol) in DMF (30 mL), chilled in an ice bath, was added EDC.HCl (2.53 g, 13.2 mmol) in two portions. The mixture was stirred at ice bath temperature for 15 min and warmed to RT for 4 hrs. The reaction mixture was diluted with H2O (100 mL) and saturated NaHCO3 (40 mL). The aqueous mixture was extracted with EtOAC (3×30 mL), acidified to pH 3 with saturated KHSO4 and extracted with EtOAc (3×30 mL). The combined organic layers were washed with H2O (2×25 mL), saturated NaCl (25 mL), dried over MgSO4, filtered and evaporated. The crude material was re-dissolved in CHCl3 and eluted through a silica gel plug with CHCl3 (100 mL) and then EtOAc (100 mL). The EtOAc fraction was evaporated and pumped to a clear oil, 2.6 g (70%), and used without further purification.

Aufarbeitung

  1. extractionThe aqueous mixture was extracted with EtOAC (3×30 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organic layers were washed with H2O (2×25 mL), saturated NaCl (25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe crude material was re-dissolved in CHCl3
  8. washeluted through a silica gel plug with CHCl3 (100 mL)
  9. customThe EtOAc fraction was evaporated
  10. customused without further purification

Quellen und Nachweise

ORD-Eintrag
ord-10ad6b1c511a486ba1fc2e1e9aec03bf
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939569B1

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