3-Amino-5-methylpyridine → Isohexane ethyl acetate

HRID 1914648Notes

Reaction equation

HRID 1914648 reaction equation
Cl[C:2]1[CH:18]=[CH:17]C(C(F)(F)F)=[CH:15][C:3]=1[C:4](N[C@H]1CC[C@H:10]([CH:13]=[O:14])CC1)=O.NC1C=NC=C(C)C=1.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=[O:33])[CH3:32].[Na+]>C(Cl)Cl>[CH3:32][CH2:31][O:33][C:13]([CH3:10])=[O:14].[CH3:17][CH2:18][CH2:2][CH:3]([CH3:15])[CH3:4]

Participants

5

Reactant 3

HCID 27628943-Amino-5-methylpyridineHCID 5049666Sodium triacetoxyborohydrideHCID 178520978HCID 178520978, compound

Product 1

HCID 21882781Isohexane ethyl acetateYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 50 mL round-bottomed flask containing trans-2-chloro-N-(4-formyl-cyclohexyl)-5-trifluoromethyl-benzamide (Ex. 1 step 3) (100 mg, 0.3 mmol) and 3-amino-5-methylpyridine (36 mg, 0.3 mmol) in dry DCM (5 mL) is added sodium triacetoxyborohydride (106 mg, 0.45 mmol) in one portion. The suspension is stirred at RT for 4 hours. The mixture is partitioned between DCM and saturated sodium bicarbonate, passed through a phase separator to recover the DCM layer and evaporated to give a colourless solid. The crude product is redissolved in DCM, absorbed directly onto silica gel and columned on silica gel using a 12 g pre-packed column and isohexane/EtOAc gradient elution (0% to 100% EtOAc). Product-containing fractions are combined and evaporated and the product is isolated as a colourless solid after trituration with 20% EtOAc/isohexane, 55 mg, [MH+426.40].

Workup

  1. customThe mixture is partitioned between DCM and saturated sodium bicarbonate
  2. customto recover the DCM layer
  3. customevaporated
  4. customto give a colourless solid
  5. customabsorbed directly onto silica gel
  6. washa 12 g pre-packed column and isohexane/EtOAc gradient elution (0% to 100% EtOAc)
  7. customevaporated

Sources & evidence

ORD record
ord-fd14ccca9a3946c797526dd07e6e5d4b
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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