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

HRID 1830749

반응식

HRID 1830749 반응식
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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-de70020df0f5406ba6baf410bb83de1b
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067506B2

연결된 노트

불러오는 중…