Hydrochloric Acid → HCID 89586491, compound

HRID 333748Notes

Reaction equation

HRID 333748 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[N:6]1[C:7]([CH2:15][CH2:16][C:17](OC)=[O:18])=[CH:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12.Cl>C(O)C.C1COCC1>[N:6]1[C:7]([CH2:15][CH2:16][CH2:17][OH:18])=[CH:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 755885HCID 755885, compoundHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 89586491HCID 89586491, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, to a solution of calcium chloride (268 mg) in ethanol (4 mL) were added THF (2.8 mL) and sodium tetrahydroborate (183 mg) and the mixture was stirred at 0° C. for 30 min. Then, a solution of methyl 3-imidazo[1,2-a]pyridin-2-ylpropanoate (395 mg) in THF (1.2 mL) was added dropwise, and the mixture was allowed to warm to room temperature and stirred for 18 hr. Under ice-cooling, to the reaction mixture was added 1N hydrochloric acid (4.84 mL), and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (223 mg).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 18 hr
  3. temperatureUnder ice-cooling, to the reaction mixture
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-3eacdcea33de455882702ed13ef9a373
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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