Methyl 1,2,3,4-tetrahydro-3-quinolinecarboxylate → (1,2,3,4-Tetrahydroquinolin-3-yl)methanol

HRID 1821764

Reaktionsgleichung

Reaktionsgleichung von HRID 1821764
C[O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH2:6]1)=O>CCOCC>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH:5]([CH2:3][OH:2])[CH2:6]1

Komponenten

3

Edukt 1

HCID 283526Methyl 1,2,3,4-tetrahydro-3-quinolinecarboxylate

Produkt 1

HCID 12662987(1,2,3,4-Tetrahydroquinolin-3-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred solution of the 1,2,3,4-Tetrahydro-quinoline-3-carboxylic acid methyl ester (93 mg, 0.49 mmol) in 1.5 mL of Et2O at 0° C. under nitrogen was added LiAIH4 (1M in Et2O) dropwise with vigorous gas evolution and a white precipitate formation. After 30 min., the reaction was carefully quenched with 15% NaOH (3 mL) and 3 mL of Et2O was added and the mixture stirred rapidly at RT for 15 min. The layers were separated and the aqueous layer extracted (1×10 mL) with Et2O. The organics were combined, dried (MgSO4), filtered and concentrated to the alcohol (64 mg, 80%). 1H-NMR (400 MHz, CDCl3) δ 6.97 (m, 2H), 6.62 (dd, 1H), 6.47 (d, 1H), 3.66 (m, 1H), 3.58 (m, 1H), 3.40 (m, 1H), 3.08 (m, 1H), 2.82 (m, 1H), 2.53 (m, 1H), 2.18 (m, 1H).

Aufarbeitung

  1. customthe reaction was carefully quenched with 15% NaOH (3 mL) and 3 mL of Et2O
  2. additionwas added
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted (1×10 mL) with Et2O
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to the alcohol (64 mg, 80%)

Quellen und Nachweise

ORD-Eintrag
ord-859ea2becbb34bfb923c5ae704696c1d
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608618B2

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