Cyclohexanone → 2-[4-(Cyclohexylamino)-2-fluoro-phenyl]propionic acid

HRID 1506862Notes

Reaction equation

HRID 1506862 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:13])[C:9]([O:11]C)=[O:10])=[C:4]([F:14])[CH:3]=1.[C:15]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[BH3-]C#N.[Na+]>CO.C(O)(=O)C>[CH:15]1([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:13])[C:9]([OH:11])=[O:10])=[C:4]([F:14])[CH:3]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 13758005Methyl 2-(4-amino-2-fluorophenyl)propanoate

Product 1

HCID 601555302-[4-(Cyclohexylamino)-2-fluoro-phenyl]propionic acidYield 67.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of compound (7) (1.50 g, 7.6 mmol), cyclohexanone (1.57 mL, 15.2 mmol), and NaBH3CN (0.96 g, 15.2 mmol) in methanol (10 mL) and acetic acid (0.2 mL) was allowed to undergo conventional reactions, followed by the same reactions and treatments as those in Example 3. The obtained crude product was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution followed by conventional hydrolysis to give 1.37 g (65%) of compound (11b) of interest as brown powder.

Workup

  1. customThe obtained crude product
  2. washwas subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution
  3. customfollowed by conventional hydrolysis

Sources & evidence

ORD record
ord-84578d2a72f24aa39ce88e41822c8e76
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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