Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2S,5R/S)-1-(tert-Butoxycarbonyl)-5-ethoxypyrrolidine-2-carboxylic acid tert-butyl ester

HRID 884387

Reaktionsgleichung

Reaktionsgleichung von HRID 884387
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH:10]([OH:13])[N:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH:10]([O:13][CH2:21][CH3:22])[N:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11077035Di-tert-butyl (s)-5-hydroxypyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 123363996(2S,5R/S)-1-(tert-Butoxycarbonyl)-5-ethoxypyrrolidine-2-carboxylic acid tert-butyl esterAusbeute 5.062,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 12.1 g of 207 (42.1 mmol) in 100 ml of anhydrous EtOH was added with 200 mg of PPTS (0.80 mmol, 1.9 mole %) and stirred at RT overnight. Thereafter, the solvent was completely removed under vacuum, and the residue was taken up in 250 ml of a 1:2 mixture of EE/CH. After filtration over a short silica gel column, the eluate was concentrated to obtain 12.8 g of α-methoxycarbamate 45 (40.5 mmol, 96%) as a slightly yellowish oil. An analytical sample was obtained by column chromatography over silica gel (EE/CH 1:2).

Aufarbeitung

  1. customThereafter, the solvent was completely removed under vacuum
  2. additionthe residue was taken up in 250 ml of a 1:2 mixture of EE/CH
  3. filtrationAfter filtration over a short silica gel column
  4. concentrationthe eluate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-a496044c6a3d48c098aad75aba7a0889
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242105B2

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