3-(4-(Dibenzylamino)-2-fluorophenyl)oxetan-3-ol → 3-(4-Amino-2-fluorophenyl)oxetan-3-ol

HRID 1842918Notes

Reaction equation

HRID 1842918 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2([OH:19])[CH2:18][O:17][CH2:16]2)=[C:11]([F:20])[CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([OH:19])[CH2:16][O:17][CH2:18]2)=[C:11]([F:20])[CH:10]=1

Participants

4

Reactant 1

HCID 708168813-(4-(Dibenzylamino)-2-fluorophenyl)oxetan-3-ol

Product 1

HCID 866721503-(4-Amino-2-fluorophenyl)oxetan-3-olYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-(4-(dibenzylamino)-2-fluorophenyl)oxetan-3-ol (2.15 g, 5.92 mmol, 1.0 eq) in THF (125 mL) was added 10% Pd/C (0.230 g) under argon and stirred under hydrogen balloon pressure for 16 h. The mixture was passed through celite, and the filtrate concentrated under vacuum. The resulting crude product was purified by CC using EtOAc/PE (7:3) to get 3-(4-amino-2-fluorophenyl)oxetan-3-ol (0.9 g, 73%; TLC system: EtOAc 100%, 0.5).

Workup

  1. concentrationthe filtrate concentrated under vacuum
  2. customThe resulting crude product was purified by CC

Sources & evidence

ORD record
ord-9251316714354502bae4dee21df605ed
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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