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

HRID 1842909ノート

反応式

HRID 1842909 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-05b7b2c25df940ce8f87de4804a31548
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

読み込み中…