Hydrochloric Acid → 2-(2-(3,4-Diethoxybenzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetic Acid

HRID 515720Notes

Reaction equation

HRID 515720 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][C:30]=1[O:31][CH2:32][CH3:33])[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]1[CH2:18][CH2:19][CH2:20][CH:21]([CH2:22][C:23]([O:25]CC)=[O:24])[C:13]1=[CH:12]2)[CH3:2].[Li+].[OH-].Cl>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][C:30]=1[O:31][CH2:32][CH3:33])[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]1[CH2:18][CH2:19][CH2:20][CH:21]([CH2:22][C:23]([OH:25])=[O:24])[C:13]1=[CH:12]2)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67250738Ethyl 2-(2-(3,4-Diethoxybenzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate

Product 1

HCID 583296082-(2-(3,4-Diethoxybenzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetic AcidYield 88.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of ethyl 2-(2-(3,4-diethoxybenzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate (0.100 g, 0.221 mmol) in 1,4-dioxane (4 mL) was added 1.0 M LiOH (aq) (1.107 mL, 1.107 mmol). The reaction was stirred at 23° C. for 16 h in a 20 mL sealed scintillation vial. The mixture was poured into 1 M HCl and extracted with EtOAc (3×5 mL). The organic layers were combined, dried over MgSO4, and filtered by vacuum filtration through a glass fiber paper. The solvent was removed under reduced pressure to give the title compound (0.0831 g) as a tan solid. LCMS m/z=424.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27-1.36 (m, 6H), 1.49 (d, J=11.37 Hz, 1H), 1.87-1.95 (m, 1H), 1.99-2.07 (m, 1H), 2.07-2.16 (m, 1H), 2.40-2.49 (m, 1H), 2.77-2.87 (m, 1H), 3.24-3.35 (m, 1H), 3.73-3.84 (m, 1H), 3.96-4.06 (m, 4H), 4.07-4.16 (m, 1H), 4.96 (s, 2H), 6.14 (s, 1H), 6.76 (dd, J=8.78, 2.34 Hz, 1H), 6.88-6.96 (m, 2H), 7.01-7.07 (m, 2H), 7.21 (d, J=8.84 Hz, 1H), 12.27 (s, 1H).

Workup

  1. customsealed scintillation vial
  2. extractionextracted with EtOAc (3×5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered by vacuum filtration through a glass fiber paper
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2c1f71d1406e41c0b19a62d7cc89bd27
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

Loading…