Pyridine → Phenyl 3-fluoro-4-(3-hydroxyazetidin-1-yl)phenylcarbamate

HRID 1842995Notes

Reaction equation

HRID 1842995 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)=[C:4]([F:13])[CH:3]=1.N1C=CC=CC=1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>CC(C)=O>[F:13][C:4]1[CH:3]=[C:2]([NH:1][C:21](=[O:22])[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:9][CH:10]([OH:12])[CH2:11]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 866721701-(4-Amino-2-fluorophenyl)azetidin-3-ol

Product 1

HCID 86672171Phenyl 3-fluoro-4-(3-hydroxyazetidin-1-yl)phenylcarbamateYield 76.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-(4-amino-2-fluorophenyl)azetidin-3-ol (1.8 g, 9.94 mmol, 1.0 eq) in acetone (50 mL) was added pyridine (1.57 g, 19.87 mmol, 2.0 eq) and phenyl chloroformate (1.71 g, 10.89 mmol, 1.1 eq) and stirred at RT for 2 h. The reaction mixture was evaporated, diluted with EtOAc (100 mL), washed with water (100 mL) followed by brine and evaporated. The residue obtained was purified by CC (eluent: EtOAc/PE (1:4)) to obtain phenyl 3-fluoro-4-(3-hydroxyazetidin-1-yl)phenylcarbamate (2.3 g, 76%, brown solid) (TLC: EtOAc/PE (1:1), Rf: 0.45).

Workup

  1. customThe reaction mixture was evaporated
  2. additiondiluted with EtOAc (100 mL)
  3. washwashed with water (100 mL)
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by CC (eluent: EtOAc/PE (1:4))

Sources & evidence

ORD record
ord-6441a7ed97254305a6eafc74a3fa8730
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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