Sodium borohydride → rel-(1R,5R)-5-Methyl-3-(3-nitro-4-pyridinyl)-2-cyclohexen-1-ol

HRID 705244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705244
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1.[BH4-].[Na+]>CCO>[CH3:1][C@@H:2]1[CH2:7][C@H:6]([OH:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 592265435-Methyl-3-(3-nitro-4-pyridinyl)-2-cyclohexen-1-one

Produkt 1

HCID 59226572rel-(1R,5R)-5-Methyl-3-(3-nitro-4-pyridinyl)-2-cyclohexen-1-olAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone (1.0 equiv.) in EtOH (0.3 M) was added CeCl3-7H2O (1.2 equiv.). The reaction was cooled to 0° C., then NaBH4 (1.2 equiv.) was added in portions. Stirred for 1 h at 0° C., then quenched by adding water, concentrated to remove the EtOH, added EtOAc, extracted the organics, washed with brine, then dried with Na2SO4, filtered and concentrated to yield cis-(+/−)-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (94%). LC/MS=235.2 (M+H), LC=2.62 min.

Aufarbeitung

  1. customquenched
  2. additionby adding water
  3. concentrationconcentrated
  4. customto remove the EtOH
  5. additionadded EtOAc
  6. extractionextracted the organics,
  7. washwashed with brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-97bd42a2163641ccad2dc7f69423f504
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173883B2

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