Lithium borohydride → (R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamate

HRID 7286

Reaktionsgleichung

Reaktionsgleichung von HRID 7286
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][CH2:17][C:18]([O-])=[O:19])[C:13]([O-])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+]>C1COCC1.[Cl-].[Na+].O.O>[OH:19][CH2:18][CH2:17][CH2:16][C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][OH:14]

Komponenten

6

Edukt 2

HCID 4148881Lithium borohydrideHCID 22017142[((Benzyloxy)carbonyl]amino}pentanedioate

Produkt 1

HCID 2757382(R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamateAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of dimethyl (2R)-2-{[((benzyloxy)carbonyl]amino}pentanedioate (22.4 g) in dry THF (74 ml) was added dropwise over 1 h to a stirred mixture of lithium borohydride (4.5 g) in THF (200 ml) at room temperature, under nitrogen. Stirring at room temperature was continued for 3 days. The reaction mixture was diluted with brine and water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (16.5 g) as a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (over magnesium sulphate)
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0716b8127315465ca5bb1dda1907bd78
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084139B2

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