Methanol → HCID 58065839, compound

HRID 62163Notes

Reaction equation

HRID 62163 reaction equation
[OH:1][CH:2]([CH2:23][NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1)[CH2:3][N:4]1[C:12]2[CH:11]=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[C:6]2[CH2:14][N:15]([C:18](OCC)=O)[CH2:16][CH2:17][C:5]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].CO>C1COCC1>[CH3:18][N:15]1[CH2:16][CH2:17][C:5]2[N:4]([CH2:3][CH:2]([OH:1])[CH2:23][NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=3)[C:12]3[CH:11]=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=3[C:6]=2[CH2:14]1

Participants

5

Reactant 3

HCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 46851210Ethyl 5-(2-Hydroxy-3-(3-methoxyphenylamino)propyl)-8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 58065839HCID 58065839, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Following a literature procedure (Zoidis et al., Bioorg. Med. Chem. 2009, 17, 1534-1541), the title compound of Example 18 (0.015 g, 0.034 mmol) was dissolved in anhydrous THF (0.34 mL) and cooled to 0° C. A solution of LAH (0.10 mL, 1.0 M in THF) was added dropwise, and the reaction was stirred for 2 h at 0° C. MeOH was added to quench the remaining LAH and after 45 min, the mixture was partitioned between EtOAc/H2O. The organic layer was separated and the aqueous layer was extracted with EtOAc (3×), and the combined organic layers were washed with satd. aq. NaCl, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by column chromatography (SiO2, 0-20% MeOH/Acetone+1% Et3N), followed by PTLC (10% MeOH/Acetone+1% Et3N) to afford the desired product (0.6 mg, 5%).

Workup

  1. customto quench the remaining LAH
  2. waitafter 45 min
  3. customthe mixture was partitioned between EtOAc/H2O
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×)
  6. washthe combined organic layers were washed with satd
  7. dry with materialaq. NaCl, dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was purified by column chromatography (SiO2, 0-20% MeOH/Acetone+1% Et3N)

Sources & evidence

ORD record
ord-fc971175a0eb4502ba73b2fc6eef32c1
Source dataset
uspto-grants-2016_09
Patent number
US09446022B2

Reaction notes

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