Pyridine → Phenyl 3-fluoro-4-(1-hydroxycyclopropyl)phenylcarbamate

HRID 1842909Notes

Reaction equation

HRID 1842909 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:11])[CH2:10][CH2:9]2)=[C:4]([F:12])[CH:3]=1.N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>CC(C)=O>[F:12][C:4]1[CH:3]=[C:2]([NH:1][C:20](=[O:21])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=[CH:6][C:5]=1[C:8]1([OH:11])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866721471-(4-Amino-2-fluorophenyl)cyclopropanol

Product 1

HCID 86672145Phenyl 3-fluoro-4-(1-hydroxycyclopropyl)phenylcarbamateYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-(4-amino-2-fluorophenyl)cyclopropanol (0.7 mg, 4.19 mmol, 1.0 eq) in acetone (10 mL) was added pyridine (0.33 mL, 4.19 mmol, 1.0 eq) and phenyl chloroformate (0.5 mL, 4.19 mmol, 1.0 eq) and stirred at 0° C. to RT for 1 h. The solvent was evaporated, the residue diluted with water (10 mL×2), extracted with EtOAc (25 mL), brine (10 mL) and dried over Na2SO4 and evaporated under vacuum; the resulting residue was purified by CC using EtOAc/PE (1:4 as eluent to get phenyl 3-fluoro-4-(1-hydroxycyclopropyl)phenylcarbamate (0.9 g, 75%, off white solid; TLC system: EtOAc/PE (1:1), Rf: 0.6).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with water (10 mL×2)
  3. extractionextracted with EtOAc (25 mL), brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum
  6. customthe resulting residue was purified by CC

Sources & evidence

ORD record
ord-05b7b2c25df940ce8f87de4804a31548
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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