Aluminium lithium hydride → (S)-(1-Formyl-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester

HRID 990398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990398
[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:9]([C:14](=[O:19])N(OC)C)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:9]([CH:14]=[O:19])[CH2:10][CH:11]([CH3:12])[CH3:13])[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 53718737(S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester

Produkt 1

HCID 54220075(S)-(1-Formyl-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester (288 mg, 1.0 mmol) was dissolved in Et2O (10 mL), cooled to 0° C., treated with LAH (38 mg, 1.0 mmol), and stirred cold for 30 minutes. The reaction was quenched by dropwise addition of a solution of 150 mg Na2S2O3 in 5 mL H2O. The reaction was diluted with H2O (100 mL), washed with Et2O (3×100 mL), then the organic layers were combined, washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give the desired product which was carried on immediately without further purification.

Aufarbeitung

  1. customThe reaction was quenched by dropwise addition of a solution of 150 mg Na2S2O3 in 5 mL H2O
  2. additionThe reaction was diluted with H2O (100 mL)
  3. washwashed with Et2O (3×100 mL)
  4. washwashed with saturated bicarbonate solution and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5309e48acc1d49b89c642ed76a99e323
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458781B1

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