Sodium Thiosulfate → Tert-butyl 3-methyl-1-oxobutan-2-ylcarbamate

HRID 1951243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1951243
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([NH:30][C@H:31]([CH2:35][OH:36])[CH:32]([CH3:34])[CH3:33])([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.C(OCC)C>[C:26]([O:25][C:23](=[O:24])[NH:30][CH:31]([CH:35]=[O:36])[CH:32]([CH3:33])[CH3:34])([CH3:27])([CH3:29])[CH3:28]

Komponenten

7

Edukt 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 7021464tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

Produkt 1

HCID 545985Tert-butyl 3-methyl-1-oxobutan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of Dess-Martin periodinane (3.12 g, 0.0073 mol, 1.5 eq) in dichloromethane (25 mL) was added a solution of N-Boc-L-valinol (1 g, 0.0049 mol, 1 eq) in dichloromethane (25 mL). The reaction mixture was stirred at room temperature for 3 h and was diluted with diethyl ether (50 mL). The mixture was poured into an aqueous saturated solution of sodium bicarbonate (100 mL) containing sodium thiosulfate (8.16 g, 10.5 eq). The mixture was stirred for 30 min and the layers were separated. The ether layer was washed with an aqueous saturated solution of sodium bicarbonate (50 mL), water (50 mL), dried (sodium sulfate) and filtered. The filtrate was concentrated to give the crude (1-formyl-2-methyl-propyl)-carbamic acid tert-butyl ester used for the next step without further purification.

Aufarbeitung

  1. stirringThe mixture was stirred for 30 min
  2. customthe layers were separated
  3. washThe ether layer was washed with an aqueous saturated solution of sodium bicarbonate (50 mL), water (50 mL)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-84d75cb4f1aa49e59b2d30e6c39fd674
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404693B2

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