Formaldehyde → Dimethyl (3R,4S)-1-benzylpyrrolidine-3,4-dicarboxylate

HRID 478776

Reaktionsgleichung

Reaktionsgleichung von HRID 478776
[CH2:1]([NH:8][CH2:9]C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([O:21][CH3:22])(=[O:20])/[CH:14]=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].C=O.[CH3:25]CN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][C@H:15]([C:16]([O:18][CH3:19])=[O:17])[C@H:14]([C:13]([O:21][CH3:22])=[O:20])[CH2:25]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 869652-(Benzylamino)acetic acidHCID 5271565Dimethyl maleate

Produkt 1

HCID 10978757Dimethyl (3R,4S)-1-benzylpyrrolidine-3,4-dicarboxylateAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of N-benzylglycine (12.39 g, 75 mmol), dimethyl maleate (6.26 g, 50 mmol), paraformaldehyde (4.5 g, 150 mmol) and DIEA (8.7 mL, 50 mmol) in toluene (100 mL) was stirred at reflux for 2 hours and concentrated. The residue was taken up in EtOAc. The solution was washed with brine 3×, dried (MgSO4) and concentrated. Column chromatography eluting with 50% EtOAc/hexanes provided dimethyl cis-1-benzyl-3,4-pyrrolidinedicarboxylate (4.8 g, 34%). MS (M+H)+=278.5.

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated
  3. washThe solution was washed with brine 3×
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washColumn chromatography eluting with 50% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-46dd9d23806947f28dc42014a3fe4a85
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642255B2

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