Reaktion #10516

ord-2ee3358ec00f4d3a99109190e3ee13ea

Reaktionsgleichung

O=C([O-])O.[K+]
potassium bicarbonate
CCOC(=O)C[C@@H]1CC[C@@H](C(=O)OC(C)(C)C)N1C(=O)OC(C)(C)C
1d
CCOC(=O)C[C@@H]1CC[C@@H](C(=O)OC(C)(C)C)N1C(=O)OC(C)(C)C
di-tert-butyl (2S ,5S)-5-ethoxycarbonylmethylpyrrolidine-1,2-dicarboxylate
[BH4-].[Li+]
lithium borohydride
CC(C)(C)OC(=O)[C@@H]1CC[C@@H](CCO)N1C(=O)OC(C)(C)C
di-tert-butyl (2S,5S)-5-hydroxyethylpyrrolidine-1,2-dicarboxylate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe phases were separated
  2. 2
    Waschenthe organic phase was washed with 250 ml of a saturated sodium chloride solution
  3. 3
    TrocknenThe organic phase was dried with sodium sulfate
  4. 4
    Sonstigethe solvent was removed in vacuo
  5. 5
    SonstigeThe residue was chromatographed on silica gel

Vorschrift

43 g of the product from 1d were dissolved in 300 ml of diethyl ether. A solution of 3.1 g of lithium borohydride in 300 ml of diethyl ether was added dropwise thereto. The mixture was stirred for 6 h and the reaction was stopped by cautious addition of 300 ml of a saturated potassium bicarbonate solution. The phases were separated and the organic phase was washed with 250 ml of a saturated sodium chloride solution. The organic phase was dried with sodium sulfate, and the solvent was removed in vacuo. The residue was chromatographed on silica gel.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094800B2uspto-grants-2006_08