Hydrochloric Acid → 1-(4-Amino-2-fluorophenyl)cyclopropanol

HRID 1842908ノート

反応式

HRID 1842908 の反応式
[Si]([O:8][C:9]1([C:12]2[CH:31]=[CH:30][C:15]([N:16]=C(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:14][C:13]=2[F:32])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.Cl>C1COCC1>[NH2:16][C:15]1[CH:30]=[CH:31][C:12]([C:9]2([OH:8])[CH2:10][CH2:11]2)=[C:13]([F:32])[CH:14]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 866721464-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-N-(diphenylmethylene)-3-fluoroaniline

生成物 1

HCID 866721471-(4-Amino-2-fluorophenyl)cyclopropanol収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 4-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-N-(diphenylmethylene)-3-fluoroaniline (4.5 mg, 10.11 mmol, 1.0 eq) in THF (10 mL) was added 1N HCl (20 mL) and stirred vigorously for 1 h. The mixture was extracted with EtOAc (20 mL). The aqueous layer was basified with 1N aq. NaOH (30 mL) and extracted with EtOAc (50 mL). The combined organic layers were extracted with brine (20 mL) and dried over Na2SO4 and the solvent evaporated under vacuum; the resulting residue was purified by CC using EtOAc/PE (1:1) as eluent to get 1-(4-amino-2-fluorophenyl)cyclopropanol (0.7 g, 49%, yellow solid; TLC system: EtOAc/PE (1:1), Rf: 0.25).

後処理

  1. extractionThe mixture was extracted with EtOAc (20 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. extractionThe combined organic layers were extracted with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated under vacuum
  6. customthe resulting residue was purified by CC

出典と根拠

ORDレコード
ord-2f18a8112afb4a2fa51037038744176d
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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