Tetrahydrofuran → (R)-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-ol

HRID 1042640Notes

Reaction equation

HRID 1042640 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([OH:8])[CH2:3]1.C(=O)(O)[O-].[Na+].C1COCC1.F[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[N+:30]([O-:32])=[O:31]>O>[N+:30]([C:21]1[CH:22]=[C:23]([C:26]([F:27])([F:28])[F:29])[CH:24]=[CH:25][C:20]=1[N:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([OH:8])[CH2:3]1)([O-:32])=[O:31]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 516892Sodium BicarbonateHCID 2759333(3R)-piperidin-3-ol hydrochloride

Product 1

HCID 7449941(R)-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100-mL round bottom flask (RBF) was added (R)-piperidin-3-ol hydrochloride (1.29 g, 9.37 mmol), sodium bicarbonate (2.76 g, 32.8 mmol), THF and 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (1.31 ml, 9.37 mmol). The yellow mixture was heated to 75° C. with a water-cooled reflux condensor and allowed to stir 14 h. The reaction was filtered through a glass frit, rinsing with EtOAc, and concentrated in vacuo to give (R)-1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-ol as an orange oil.

Workup

  1. temperaturecooled
  2. temperaturereflux condensor
  3. filtrationThe reaction was filtered through a glass frit
  4. washrinsing with EtOAc
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5859ba85a204788a1339d688375712d
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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