(Dimethyl sulfide)trihydroboron → n[3,5-Bis(3-methoxypropyl)benzyl]cyclopropanamine

HRID 658252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658252
[CH:1]1([NH:4][C:5](=O)[C:6]2[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[C:8]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:7]=2)[CH2:3][CH2:2]1.B.CSC>C1COCC1>[CH3:21][O:20][CH2:19][CH2:18][CH2:17][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=1)[CH2:5][NH:4][CH:1]1[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 57456873N-cyclopropyl-3,5-bis(3-methoxypropyl)benzamide

Produkt 1

HCID 59234217n[3,5-Bis(3-methoxypropyl)benzyl]cyclopropanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-cyclopropyl-3,5-bis(3-methoxypropyl)benzamide (1 eq.) from the previous step in THF (0.18 M) at 80° C. was added borane-dimethylsulfide (10 eq.). The reaction was distilled to about half volume and heated under reflux for 3 h. Then, the reaction was cooled to rt and slowly quenched with 10% HCl aqueous solution. The reaction was heated to reflex again and stirred for 45 min. After cooling to rt, the reaction was diluted with EtOAc and basified with aqueous NaOH solution (pH >10). The organic extract was washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 25% EtOAc in Hex plus 3% Et3N) to afford the title compound amine 3 as an oil.

Aufarbeitung

  1. distillationThe reaction was distilled to about half volume
  2. temperatureheated
  3. temperatureunder reflux for 3 h
  4. customslowly quenched with 10% HCl aqueous solution
  5. temperatureThe reaction was heated
  6. temperatureAfter cooling to rt
  7. additionthe reaction was diluted with EtOAc and basified with aqueous NaOH solution (pH >10)
  8. extractionThe organic extract
  9. washwas washed with saturated aqueous NaHCO3, brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customThe crude product was purified by flash column chromatography (SiO2, 25% EtOAc in Hex plus 3% Et3N)

Quellen und Nachweise

ORD-Eintrag
ord-29c1838bf1864f0a83898f69620263d3
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076359B2

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