Aniline → (R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide

HRID 1797861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797861
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.[Si:12]([O:29][C@@H:30]1[CH2:34][CH2:33][O:32][C:31]1=[O:35])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C(C(C(O)=O)O)O.[K].[Na]>C(Cl)Cl>[Si:12]([O:29][C@H:30]([CH2:34][CH2:33][OH:32])[C:31]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:35])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 6115AnilineHCID 16682925TrimethylaluminumHCID 53797635(R)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-oneHCID 86590012HCID 86590012, Verbindung

Produkt 1

HCID 59593434(R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamideAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of aniline (356 mg, 348 μL, 3.82 mmol) in DCM (17 mL) was added trimethylaluminum (2.0M, 2.1 mL, 4.2 mmol) dropwise and the reaction mixture was stirred at RT for 40 min. A solution of (R)-3-(tert-butyldiphenylsilyloxy)-dihydrofuran-2(3H)-one (1.00 g, 2.94 mmol) in DCM (12 mL) was added dropwise and the reaction mixture was stirred at RT for 16 hours. The reaction mixture was poured into a saturated solution of sodium potassium tartaric acid and stirred for 15 min. The layers were separated, and the aqueous layer was washed with DCM (4×). The combined organics were washed with 0.1M HCl (2×), brine, dried over Na2SO4 and evaporated to dryness. Purification by silica gel chromatography (10-30% EtOAc in hexane) afforded the (R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide (1.00 g, 78%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=434.7; tR=2.16 min.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at RT for 16 hours
  2. stirringstirred for 15 min
  3. customThe layers were separated
  4. washthe aqueous layer was washed with DCM (4×)
  5. washThe combined organics were washed with 0.1M HCl (2×), brine
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customPurification by silica gel chromatography (10-30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0defb71c850444a991af8b145cdd8207
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343763B2

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