diethyl (3S,4S)-1-benzylpyrrolidine-3,4-dicarboxylate → (3R,4R)-1-tert-butyl 3,4-diethyl pyrrolidine-1,3,4-tricarboxylate

HRID 1158344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158344
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][N:8](CC2C=CC=CC=2)[CH2:7]1)=[O:5])[CH3:2].C(O[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])(C)(C)C>CCO.[Pd]>[CH2:14]([O:13][C:11]([C@H:10]1[C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][N:8]([C:28]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:34])[CH2:9]1)=[O:12])[CH3:15]

Komponenten

5

Edukt 2

HCID 6558921diethyl (3S,4S)-1-benzylpyrrolidine-3,4-dicarboxylateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Produkt 1

HCID 59512444(3R,4R)-1-tert-butyl 3,4-diethyl pyrrolidine-1,3,4-tricarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of (3S*,4S*)-1-benzyl-pyrrolidine-3,4-dicarboxylic acid diethyl ester (82.8 g, 271.14 mmol), di-tert-butylcarbonate (88.76 g, 406.71 mmol) and Pd/C 10% (8 g) in EtOH (1.5 L) is stirred under hydrogen atmosphere. The crude material is filtered over a pad of Celite and concentrated. The crude material is purified by flash chromatography on silica gel (eluent: CH2Cl2/acetone 100:0 to 95:5). TLC, Rf (CH2Cl2/acetone 95:5)=0.51. MS (LC-MS): 216.2 [M+H-Boc]+.

Aufarbeitung

  1. filtrationThe crude material is filtered over a pad of Celite
  2. concentrationconcentrated
  3. customThe crude material is purified by flash chromatography on silica gel (eluent: CH2Cl2/acetone 100:0 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-742de50f04fd483b9247bf151cc6039e
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

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