Acetic Acid → HCID 70873966, compound

HRID 2208721Notes

Reaction equation

HRID 2208721 reaction equation
[NH2:1][C:2]1[C:3]([CH3:16])=[C:4]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:17]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:17]1([NH:1][C:2]2[C:3]([CH3:16])=[C:4]([CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 68295733Methyl 3-amino-2-methyl-5-(trifluoromethyl)benzoate

Product 1

HCID 70873966HCID 70873966, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-2-methyl-5-(trifluoromethyl)benzoate (2.5 g, 10.7 mmol) and cyclopentanone (4.5 g, 53.49 mmol) in methanol (25 mL) was added acetic acid (1.98 g, 21.44 mmol). After 3 h, sodium cyanoborohydride (1.68 g, 24.3 mmol) was added and the reaction stirred overnight. On completion, the solvent was removed under reduced pressure and crude material was purified by column chromatography to afford methyl 3-(cyclopentylamino)-2-methyl-5-(trifluoromethyl)benzoate (1.8 g, 55.9%).

Workup

  1. customOn completion, the solvent was removed under reduced pressure and crude material
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-cd6c3a9d478344ac8143cc62fe0edd27
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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