Dimethyl Sulfide → Tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1354846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354846
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].S(C)C.CO.C(Cl)(Cl)Cl>C1COCC1>[C:13]([O:12][C:10]([N:5]1[CH2:6][CH:7]([OH:9])[CH2:8][CH:4]1[CH2:3][OH:2])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 21584188Chloroform methanol

Produkt 1

HCID 4204845Tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of N-Boc-hydroxyproline-methyl ester (343) (15 g, 65 mmol) in THF (70 mL) was added BH3.SMe2 (55 mL, 2.0 M in Et2O, 110 mmol). The solution was heated to reflux with stirring for four hours and reaction progress was monitored by TLC (5% MeOH/CHCl3, product had lower Rf than starting material, stained with K2MnO4). The heat was removed and the reaction was quenched by the slow addition of MeOH (40 mL). The resulting solution was heated to reflux again for 45 minutes, allowed to cool and concentrated to yield an oil that was purified by flash chromatography (1–15% MeOH in CHCl3) to give 12.68 g (˜90% yield) of the desired product (344).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. customreaction progress
  4. customThe heat was removed
  5. customthe reaction was quenched by the slow addition of MeOH (40 mL)
  6. temperatureThe resulting solution was heated
  7. temperatureto reflux again for 45 minutes
  8. temperatureto cool
  9. concentrationconcentrated
  10. customto yield an oil that
  11. customwas purified by flash chromatography (1–15% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-fa42f683c5244ce49ff57c24d7c241f6
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223759B2

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