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

HRID 1830749

反応式

HRID 1830749 の反応式
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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-de70020df0f5406ba6baf410bb83de1b
出典データセット
uspto-grants-2006_06
特許番号
US07067506B2

関連ノート

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