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

HRID 1842908노트

반응식

HRID 1842908 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 866721471-(4-Amino-2-fluorophenyl)cyclopropanol수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2f18a8112afb4a2fa51037038744176d
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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