Sodium sulfate decahydrate → 3-(7-Methoxy-indol-1-yl)-3-pyridin-3-yl-propan-1-ol

HRID 250210Notes

Reaction equation

HRID 250210 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[O:21][CH3:22])[CH:14]=[CH:13]1)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:22][O:21][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[N:12]([CH:5]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:4][CH2:3][OH:2])[CH:13]=[CH:14]2

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 580884263-(7-Methoxy-indol-1-yl)-3-pyridin-3-yl-propionic acid methyl ester

Product 1

HCID 580884743-(7-Methoxy-indol-1-yl)-3-pyridin-3-yl-propan-1-olYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(7-methoxy-indol-1-yl)-3-pyridin-3-yl-propionic acid methyl ester (0.290 g) in THF (10 ml) was added a solution of lithium aluminum hydride (1 M in THF, 1 ml) at 0° C. The reaction mixture was stirred for 2 hours at room temperature. To the solution was added sodium sulfate decahydrate (1 g) and stirring was continued until no more bubbling was observed. The suspension was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica gel eluting with ethyl acetate to give 3-(7-methoxy-indol-1-yl)-3-pyridin-3-yl-propan-1-ol (0.178 g) as an oil, (M+H=283).

Workup

  1. stirringstirring
  2. customno more bubbling
  3. filtrationThe suspension was filtered through Celite
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-7ac78f64f6e1439f9b7432fdf661b81e
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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