Triphenylphosphine → Tert-butyl 4-(2-(4-bromo-2-(trifluoromethyl)phenoxy)ethyl)piperidine-1-carboxylate

HRID 517937Notes

Reaction equation

HRID 517937 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([C:42]([F:45])([F:44])[F:43])[CH:36]=1.O[CH2:47][CH2:48][CH:49]1[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][CH2:50]1>C(Cl)Cl>[Br:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:47][CH2:48][CH:49]2[CH2:50][CH2:51][N:52]([C:55]([O:57][C:58]([CH3:59])([CH3:61])[CH3:60])=[O:56])[CH2:53][CH2:54]2)=[C:37]([C:42]([F:43])([F:44])[F:45])[CH:36]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 142784o-Cresol, 4-bromo-alpha,alpha,alpha-trifluoro-HCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 67294273Tert-butyl 4-(2-(4-bromo-2-(trifluoromethyl)phenoxy)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIAD (33.5 g) was added dropwise to the solution of triphenylphosphine (43.5 g), 4-bromo-2-trifluoromethylphenol (40 g) and tert-butyl 4-(2-hydroxyethyl)-piperidine-1-carboxylate (31.7 g) in DCM (200 ml) at 0° C. during 15 minutes. The mixture was then stirred at room temperature for 20 hours. After removal of DCM under reduced pressure, to the residue was added ether (100 ml) and heptane (300 ml), solid was then filtered off. Filtrate was then washed with 1M sodium hydroxide (100 ml×3). Organic layer dried over sodium sulphate, solvent removed under vacuum, residue was then columned on silica gel using heptane:EtOAc (5:1) as eluant to give tert-butyl 4-(2-(4-bromo-2-(trifluoromethyl)phenoxy)ethyl)piperidine-1-carboxylate as a colorless oil as product (61.3 g).

Workup

  1. customAfter removal of DCM under reduced pressure
  2. additionto the residue was added ether (100 ml) and heptane (300 ml), solid
  3. filtrationwas then filtered off
  4. washFiltrate was then washed with 1M sodium hydroxide (100 ml×3)
  5. dry with materialOrganic layer dried over sodium sulphate, solvent
  6. customremoved under vacuum, residue

Sources & evidence

ORD record
ord-397246aa07b34753bc7c02ee9f38aeec
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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