Methanol → 2-[4-(Cyclopentylamino)-2-fluoro-phenyl]propionic acid

HRID 1506861Notes

Reaction equation

HRID 1506861 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.CO.[C:17]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18]1.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH:17]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)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 13758005Methyl 2-(4-amino-2-fluorophenyl)propanoate

Product 1

HCID 601555292-[4-(Cyclopentylamino)-2-fluoro-phenyl]propionic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.50 g (7.6 mmol) of compound (7) in a solvent mixture of 10 mL of methanol and 0.2 mL of acetic acid, 1.4 mL (15.2 mmol) of cyclopentanone and 0.96 g (15.2 mmol) of sodium cyanoborohydride (NaBH3CN) were added. The obtained solution was stirred at room temperature for 12 hours. Next, the reaction mixture was dried under a vacuum and extracted with dichloromethane, followed by drying over anhydrous sodium sulfate and subsequent filtration. The filtrate was dried under a vacuum, and the residue was purified by silica gel chromatograph (n-hexane/ethyl acetate 3:2) to give a methyl ester of compound (11a). This compound was hydrolyzed with sodium hydroxide to give 1.09 g (yield 54%) of compound (11a) of interest as brown powder.

Workup

  1. additionwere added
  2. customNext, the reaction mixture was dried under a vacuum
  3. extractionextracted with dichloromethane
  4. dry with materialby drying over anhydrous sodium sulfate and subsequent filtration
  5. customThe filtrate was dried under a vacuum
  6. customthe residue was purified by silica gel chromatograph (n-hexane/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-9cfb8d3dc354402ba1a44fdd56676d93
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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