Hydrochloric Acid → (S)-3-(Benzyl((S)-1-phenylethyl)amino)heptan-1-ol

HRID 1617137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617137
[CH2:1]([N:8]([C@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[C@@H:9]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1.CO.Cl>C1COCC1>[CH2:1]([N:8]([C@H:18]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:19])[C@@H:9]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 68414644(S)-3-(Benzyl((S)-1-phenylethyl)amino)heptanoic acid

Produkt 1

HCID 68752972(S)-3-(Benzyl((S)-1-phenylethyl)amino)heptan-1-olAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product from step (iii) (12 g) was dissolved in THF (120 mL) and borane-tetrahydrofuran complex (1M in THF, 132.3 ml1) added dropwise. The reaction mixture was stirred at rt overnight then MeOH was added followed by 2M HCl (20 mL). The mixture was evaporated and the residue taken up in MeOH and purified via SCX resin and the residue was further purified via column chromatography eluting with 10-20% EtOAc in isohexane to give the subtitle compound 6 g.

Aufarbeitung

  1. customThe mixture was evaporated
  2. custompurified via SCX resin
  3. customthe residue was further purified via column chromatography
  4. washeluting with 10-20% EtOAc in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-3b3242bb291c4f2db5c0e038618d98c9
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765939B2

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