Methyl iodide → N-BOC-2-methyl-4-(S)-phenyl-(L)-proline, methyl ester

HRID 496234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496234
[C:1]([N:8]1[CH2:16][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][C@H:9]1[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[CH3:24][Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1>[C:1]([N:8]1[CH2:16][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][C@@:9]1([CH3:24])[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 580029141-(tert-Butyl) 2-methyl (2S,4S)-4-phenylpyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 131725143N-BOC-2-methyl-4-(S)-phenyl-(L)-proline, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of N-BOC-4-(S)-phenyl-(L)-proline, methyl ester from Step A (2.0 g, 6.56 mmol) in anhydrous THF (20 mL) at −78° C. was added over a 30 min period 1M LiHMDS in hexanes (9.83 mL, 9.83 mmol) and allowed to stir for 30 mins at −78° C. The reaction was then allowed to stir for 1 hr at 0° C. The reaction was then cooled to −78° C. and MeI (4.65 g, 32.79 mmol) was added dropwise. The reaction was allowed to warm to rt overnight. The reaction was quenched with NH4Cl. The organic layer was collected and washed with 1M HCl, NaHCO3, brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel eluted with 75% Et2O/hexanes to give 1.85 g of desired product.

Aufarbeitung

  1. stirringto stir for 1 hr at 0° C
  2. temperatureThe reaction was then cooled to −78° C.
  3. temperatureto warm to rt overnight
  4. customThe reaction was quenched with NH4Cl
  5. customThe organic layer was collected
  6. washwashed with 1M HCl, NaHCO3, brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash column chromatography on silica gel
  10. washeluted with 75% Et2O/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f889c88ca0774d68bcbae257962622fd
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943180B2

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