Sodium borohydride → 7-[(4S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]heptanenitrile

HRID 2215079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215079
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C@@H:13]([C:14](OC)=[O:15])[CH2:12][O:11][C:10]1=[O:18])#[N:2].[BH4-].[Na+]>C(O)C>[OH:15][CH2:14][C@H:13]1[CH2:12][O:11][C:10](=[O:18])[N:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:1]#[N:2]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 69659745methyl(4R)-3-(6-cyanohexyl)-2-oxo-1,3-oxazolidine-4-carboxylate

Produkt 1

HCID 696010767-[(4S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]heptanenitrileAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ester 2-2 (560 mg) in ethanol (5 mL) at 0° C. was added NaBH4 (38 mg) and the mixture was stirred at the temperature for 1 h and quenched with half saturated NaCl. The mixture was concentrated in vacuo to remove the ethanol and the residue was extracted with ethyl acetate (3×). The organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the desired alcohol 2-3 (480 mg). 1H NMR (400 MHz, acetone-d6): δ 4.33 (t, 1H), 4.20–4.12 (m, 2H), 3.96 (m, 1H), 3.79 (m, 1H), 3.65 (m, 1H), 3.40 (m, 1H), 3.17 (m, 1H), 2.47 (t, 2H), 1.70–1.35 (m, 8H).

Aufarbeitung

  1. customquenched with half saturated NaCl
  2. concentrationThe mixture was concentrated in vacuo
  3. customto remove the ethanol
  4. extractionthe residue was extracted with ethyl acetate (3×)
  5. washThe organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4605e79689aa4ba78a98d053335107b8
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109223B2

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