Sodium borohydride → HCID 22627373, compound

HRID 278131Notes

Reaction equation

HRID 278131 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[C:7]([C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[C:6]1[CH2:21][CH2:22][CH3:23].[BH4-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[C:7]([CH:16]([OH:20])[CH:17]([CH3:18])[CH3:19])=[C:6]1[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22627257HCID 22627257, compound

Product 1

HCID 22627373HCID 22627373, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carbonitrile (70 mg) in a mixture of methanol (2 ml) and tetrahydrofuran (2 ml) was added sodium borohydride (21 mg) at 25° C. After stirred at 25° C. for 2 hours, the reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give 1-(2-chlorobenzyl)-3-(1-hydroxy-2-methylpropyl)-2-propylindole-6-carbonitrile (28 mg) as pale yellow crystals.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-9a5b5f5a8ef943aaab82350bbbdb01b9
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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