Potassium borohydride → HCID 70975437, compound

HRID 1190825Notes

Reaction equation

HRID 1190825 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[C:19]([C:21](OC)=[O:22])[N:18]=[C:17]3[N:25]([CH3:38])[C:26](=[O:37])[N:27]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]#[N:36])[C:16]=23)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[K+]>C(O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[C:19]([CH2:21][OH:22])[N:18]=[C:17]3[N:25]([CH3:38])[C:26](=[O:37])[N:27]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[C:35]#[N:36])[C:16]=23)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4192641Potassium borohydrideHCID 70975508HCID 70975508, compound

Product 1

HCID 70975437HCID 70975437, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.04 g (R)-7-(3-tert-butoxycarbonylaminopiperidin-1-yl)-1-(2-cyanobenzyl)-3-methyl-5-methoxycarbonyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine (2 mmol) was dissolved in 20 mL ethanol, to which 0.42 g potassium borohydride (8 mmol) was added in an ice bath. The stirring was continued at room temperature overnight. The reaction was monitored by TLC. After the reaction was finished, it was quenched by adding water. The reaction solution was extracted with dichloromethane for three times. The organic phase was combined, washed with saturated brine, dried with anhydrous sodium sulfate, and evaporated to dryness to afford 0.84 g crude product with a yield of 85.4%.

Workup

  1. additionwas added in an ice bath
  2. customit was quenched
  3. additionby adding water
  4. extractionThe reaction solution was extracted with dichloromethane for three times
  5. washwashed with saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-46fa9e7649cf4097acd761f749fe6712
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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