Aluminium lithium hydride → 5-(2-Diethylamino-ethyl)-2-hydroxymethyl-3-trifluoromethyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 2365145Notes

Reaction equation

HRID 2365145 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[NH:20][C:19]2[CH2:18][CH2:17][N:16]([CH2:21][CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:15](=[O:28])[C:14]=2[C:13]=1[C:29]([F:32])([F:31])[F:30])=O)C>O1CCCC1>[CH2:26]([N:23]([CH2:24][CH3:25])[CH2:22][CH2:21][N:16]1[CH2:17][CH2:18][C:19]2[NH:20][C:12]([CH2:10][OH:9])=[C:13]([C:29]([F:30])([F:32])[F:31])[C:14]=2[C:15]1=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 666084425-(2-diethylamino-ethyl)-3-trifluoromethyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 666073725-(2-Diethylamino-ethyl)-2-hydroxymethyl-3-trifluoromethyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of lithium aluminum hydride (396 mg, 10.43 mmol) in 6 ml of anhydrous tetrahydrofuran was cooled down to 0° C. in an ice-water bath, added slowly dropwise with 5-(2-diethylamino-ethyl)-3-trifluoromethyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (1.63 g, 4.35 mmol) in 10 ml of tetrahydrofuran. Upon the completion of the addition, the reaction mixture was stirred at room temperature for 1 hour and filter through a pad of Celite. The filtrate was evaporated under reduced pressure to give the crude product 5-(2-diethylamino-ethyl)-2-hydroxymethyl-3-trifloromethyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (1.208 g, 83.4%) as a yellow oil which was used as such.

Workup

  1. additionUpon the completion of the addition
  2. filtrationfilter through a pad of Celite
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c530aea3c37d4d83b89b57d9a89264e0
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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