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

HRID 1830749

Reaction equation

HRID 1830749 reaction equation
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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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 LiA1H4 (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) δ6.97 (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).

Workup

  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%)

Sources & evidence

ORD record
ord-de70020df0f5406ba6baf410bb83de1b
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Linked notes

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