Sodium borohydride → N-cyclohexyl-4-(hydroxymethyl)-3-methyl-N-(1-cyclopentyl)benzamide

HRID 1463836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463836
[CH:1]1([N:7]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[C:11]([CH3:17])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([N:7]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[C:11]([CH3:17])[CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 53901059HCID 53901059, Verbindung

Produkt 1

HCID 19088660N-cyclohexyl-4-(hydroxymethyl)-3-methyl-N-(1-cyclopentyl)benzamideAusbeute 106,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The aldehyde XXXIV of Scheme K (1.70 g, 0.0052 moles) was dissolved in 20 mls of MeOH and cooled to 0° C. under argon. NaBH4 (110 mg) was added and the mixture was allowed to warm to 25° C. Excess solvent was removed under vacuum and the residue was treated with water and ethyl acetate. The organic layer was separated and dried (Na2SO4). Removal of the solvent on the rotary evaporator gave a residue which was chromatographed on silica gel using 30% ethyl acetate/hexane as the eluent to give 1.75 g (96%) of the title compound as an oil. NMR (ppm, CDCl3): 2.28 (3H, s); 4.65 (2H, s); 7.10 (1H, d, J=8 Hz); 7.15 (1 h, s); 7.30 (1 h, d, J=8 Hz).

Aufarbeitung

  1. temperatureto warm to 25° C
  2. customExcess solvent was removed under vacuum
  3. additionthe residue was treated with water and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent
  7. customon the rotary evaporator
  8. customgave a residue which
  9. customwas chromatographed on silica gel using 30% ethyl acetate/hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-6fc3af6e0bb44dfdb6b64373ea6d79fa
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302601

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