Hydrochloric Acid → HCID 44547505, compound

HRID 1517110Notes

Reaction equation

HRID 1517110 reaction equation
C[O:2][C:3]([C:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[CH:9][C:8]([CH3:21])=[C:7]([C:22]([N:24]2[CH2:29][CH2:28][CH:27]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:26][CH2:25]2)=[O:23])[N:6]=1)=O.[BH4-].[Li+].Cl.C([O-])(O)=O.[Na+]>CCO>[OH:2][CH2:3][C:5]1[N:6]=[C:7]([C:22]([N:24]2[CH2:29][CH2:28][CH:27]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:26][CH2:25]2)=[O:23])[C:8]([CH3:21])=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 57441164HCID 57441164, compound

Product 1

HCID 44547505HCID 44547505, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.24 g (0.51 mmol) of 5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester (example 45) in 5.0 ml of EtOH were added 0.093 g (4.27 mmol) of lithium borohydride in three portions. The reaction mixture was stirred at RT for 48 hours, then poured into crashed ice, the pH was reduced to 2-3 with hydrochloric acid (25%), and the mixture subsequently neutralized with solid NaHCO3. Then, it was extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1) to give 0.097 g (43%) of the title compound as light yellow solid. MS: 448.1 (MH+).

Workup

  1. additionpoured
  2. extractionThen, it was extracted twice with CH2Cl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1)

Sources & evidence

ORD record
ord-d3a1c6d1a4cf4709bd342cfca22518c4
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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