1,2-Dichloroethane → 1-(Azetidin-1-yl)-2-(3-fluoro-4-hydroxyphenyl)ethanone

HRID 1850779Notes

Reaction equation

HRID 1850779 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[O:8]C.[NH:14]1[CH2:17][CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C.C(Cl)CCl>CN(C=O)C>[N:14]1([C:11](=[O:13])[CH2:10][C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([F:1])[CH:3]=2)[CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 521176(3-Fluoro-4-methoxyphenyl)acetic acid

Product 1

HCID 708191321-(Azetidin-1-yl)-2-(3-fluoro-4-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-fluoro-4-methoxyphenyl)acetic acid (0.94 g, 5.52 mmol) in 8 ml anhydrous DMF at RT was added azetidine (0.379 g, 6.63 mmol) and N,N-diisopropylethylamine (2.89 ml, 16.6 mmol), and EDC (1.59 g, 8.29 mmol) was added into the solution and stirred at RT for 4 hrs. The residue was purified by reverse-phase HPLC (SunFire Prep C18 OBD 5 um 19×100 mm column; 10-100% acetonitrile in 0.1% formic acid in water gradient), to give the title compound. LC/MS (m/z) 210.2 (M+15)+.

Workup

  1. additionwas added into the solution
  2. customThe residue was purified by reverse-phase HPLC (SunFire Prep C18 OBD 5 um 19×100 mm column; 10-100% acetonitrile in 0.1% formic acid in water gradient)

Sources & evidence

ORD record
ord-80843db6bb6d4a9a87f7a5bd6886a38a
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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