Lithium borohydride → HCID 23003154, compound

HRID 396208Notes

Reaction equation

HRID 396208 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:25][CH2:26][CH2:27][C:28]#[N:29])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])=[CH:10][CH:9]=2)=O)C.[BH4-].[Li+]>C1COCC1>[Cl:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([Cl:23])[C:17]=1[CH2:16][O:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:25][CH2:26][CH2:27][C:28]#[N:29])[C:6]([CH2:4][OH:3])=[CH:14]2

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 70030611HCID 70030611, compound

Product 1

HCID 23003154HCID 23003154, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-cyanopropyl)-5-(2,6-dichlorobenzyloxy)-1H-indole-2-carboxylic acid ethyl ester (2.0 g, 4.64 mmol), from Example 1(c), in THF (20 mL) at room temperature was added lithium borohydride (0.25g, 11.6 mmol). The reaction was refluxed for 20 h and then quenched slowly by adding methanol until the evolution of gas ceased. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over Na2SO4. Filtration and evaporation of the solvent yielded the desired alcohol as a white solid (1.73 g, 96%). MS(ES) m/e 389.0 [M+H]+.

Workup

  1. temperatureThe reaction was refluxed for 20 h
  2. customquenched slowly
  3. additionby adding methanol until the evolution of gas
  4. customThe reaction was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-05f0dc0db0de47e28dd0f9c184fa36cc
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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