Cesium carbonate → tert-Butyl 4-(3-bromophenoxy)piperidine-1-carboxylate

HRID 531451Notes

Reaction equation

HRID 531451 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CS(O[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 115633-BromophenolHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 22492957tert-Butyl 4-(3-bromophenoxy)piperidine-1-carboxylateYield 85.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

The mixture of 3-bromophenol (2.0 g, 11.56 mmol), tert-butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate (3.87 g, 13.872 mmol) and caesium carbonate (11.27 g, 34.68 mmol) in DMF (25 ml) was heated at 65° C. for 14 hours. Cooled to RT and diluted with ether. Ether layer was washed with water and brine, dried over sodium sulphate and distilled off the solvent to afford 3.5 g (85.3% yield) of the titled product after purification with (60/120 silica gel) column chromatography using 5% ethyl acetate in hexane as eluent. MS: m/z=356.0 (M+1).

Workup

  1. temperatureCooled to RT
  2. washEther layer was washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled off the solvent

Sources & evidence

ORD record
ord-3243a15c997043c9b651214a20e6a71a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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