Sodium Hydroxide → HCID 68510193, compound

HRID 1716565Notes

Reaction equation

HRID 1716565 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[NH2:22])[CH:10]([OH:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1([CH:27]=O)[CH2:26][CH2:25]1.OOS([O-])=O.[K+].[OH-].[Na+]>O.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=3[N:22]=[C:27]2[CH:24]2[CH2:26][CH2:25]2)[CH:10]([OH:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 123114CyclopropanecarboxaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 68510433HCID 68510433, compound

Product 1

HCID 68510193HCID 68510193, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

To a solution of 4-(2-amino-4-methyl-phenylamino)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2 g, 6.23 mmol) and cyclopropanecarboxaldehyde (485 μL, 6.5 mmol) in a 3% H2O/DMF (10 mL) solution was added Oxone® (3.05 g, 4.96 mmol). The mixture was stirred for 1 h and poured into a 0.2 N NaOH solution (25 mL). After stirring for 5 minutes, the aqueous layer was extracted four times with ethyl acetate. The combined organic extracts were washed twice with water, once with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (4/1 ethyl acetate/hexanes) to yield 4-(2-cyclopropyl-5-methyl-benzoimidazol-1-yl)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (860 mg, 37%).

Workup

  1. stirringAfter stirring for 5 minutes
  2. extractionthe aqueous layer was extracted four times with ethyl acetate
  3. washThe combined organic extracts were washed twice with water, once with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (4/1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-83021569f3c9458e8cdc1ea9d2ee9b60
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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