Water → (R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

HRID 913234

Reaktionsgleichung

Reaktionsgleichung von HRID 913234
[CH2:1]([O:8][CH2:9][C@@H:10]([C:19](ON1C(=O)CCC1=O)=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>O1CCCC1>[CH2:1]([O:8][CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:19][OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 12879025Boc-Ser(Bzl)-OSu

Produkt 1

HCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanolAusbeute 104,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under an atmosphere of argon, to a solution of 2,5-dioxopyrrolidin-1-yl O-benzyl-N-t-butoxycarbonyl-L-serinate (4.41 g) in tetrahydrofuran (30 mL) was added sodium borohydride (644 mg) in ice bath and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated ammonium chloride solution and brine, dried over anhydrous magnesium sulfate and concentrated to give the title compound (3.30 g) having the following physical data.

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated ammonium chloride solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ec1ee1fbaba2488785d377fd24f509c0
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026273B2

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