Carbamate → (Quinolin-3-yl)methanol

HRID 539506

Reaktionsgleichung

Reaktionsgleichung von HRID 539506
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11](=O)([O-:13])N.[BH4-].[Na+]>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][OH:13])[CH:2]=1

Komponenten

5

Edukt 3

HCID 276Carbamate2×HCID 7047Quinoline2×HCID 4311764Sodium borohydride

Produkt 1

HCID 12662983(Quinolin-3-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Synthesis of compounds ERW1041A, B, C, D, E, and 1069 were synthesized using the methods of Choi et al. Chemistry & Biology, Volume 12, Issue 4, Pages 469-475, except the amino-acid amines are protected by a quinoline-containing carbamate. This quinoline-containing carbamate is synthesized by reducing 3-quinolylcarbaldehyde with sodium borohydride in THF followed by an aqueous workup and flash chromatography yielding 3-quinolylcarbinol. para-Nitro-phenylchloroformate is reacted with 3-quinolylcarbinol in methylene chloride and N-methyl morpholine to give a carbonate of 3-quinoline methanol and para-Nitro-phenol. After purification by flash chromatography, this carbonate is reacted with the methyl ester of the amino acid in neat DMF to give the named compounds.

Aufarbeitung

  1. customSynthesis of compounds ERW1041A, B, C, D, E, and 1069
  2. customwere synthesized
  3. customis synthesized

Quellen und Nachweise

ORD-Eintrag
ord-081ecec58c714981b4aae8a58db36932
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871718B2

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