cis-4-(4-(Benzyloxy)phenyl)-3-fluoropiperidine → cis-4-(3-Fluoropiperidin-4-yl)phenol

HRID 1507267Notes

Reaction equation

HRID 1507267 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]2[F:21])=[CH:11][CH:10]=1)C1C=CC=CC=1>CC(O)C.[Pd]>[F:21][C@H:16]1[C@@H:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:20][CH2:19][NH:18][CH2:17]1

Participants

4

Reactant 1

HCID 118207456cis-4-(4-(Benzyloxy)phenyl)-3-fluoropiperidine

Product 1

HCID 118207461cis-4-(3-Fluoropiperidin-4-yl)phenolYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To 10% Pd/C (40 mg) under nitrogen was added a solution of cis-4-(4-(benzyloxy)phenyl)-3-fluoropiperidine (140 mg, 0.49 mmol) in IPA (4 mL). The mixture was stirred under a hydrogen atmosphere using balloon pressure at rt for 2 h. The Pd/C was removed by filtration through a glass fiber filter. The filtrate was concentrated to give cis-4-(3-fluoropiperidin-4-yl)phenol (90 mg, 0.46 mmol, 94% yield). LC/MS (Method J, M+H)+=196.25, RT=0.706 min; 1H NMR (500 MHz, methanol-d4) δ 7.14 (d, J=8.4 Hz, 2H), 6.74 (d, J=8.7 Hz, 2H), 4.63 (d, J=48.4 Hz, 1H), 3.30-3.22 (m, 1H), 3.15 (dt, J=13.1, 2.0 Hz, 1H), 2.95-2.66 (m, 3H), 2.12 (qd, J=13.0, 4.2 Hz, 1H), 1.64 (dd, J=13.4, 3.0 Hz, 1H).

Workup

  1. customat rt
  2. customfor 2 h
  3. customThe Pd/C was removed by filtration through a glass fiber
  4. filtrationfilter
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-35b55698b25a4b01918e5de32fa7e76f
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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