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

HRID 1842908Notes

Reaction equation

HRID 1842908 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2f18a8112afb4a2fa51037038744176d
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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