4-Phenylcyclohexanone → Tert-butyl[3-(1-hydroxy-4-phenylcyclohexyl)pyridin-2-yl]carbamate

HRID 1622786Notes

Reaction equation

HRID 1622786 reaction equation
Br[C:2]1[C:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[C:21]1([CH:27]2[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[C:11]([O:10][C:9](=[O:15])[NH:8][C:3]1[C:2]([C:30]2([OH:33])[CH2:29][CH2:28][CH:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:32][CH2:31]2)=[CH:7][CH:6]=[CH:5][N:4]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 786054-PhenylcyclohexanoneHCID 19704035tert-Butyl (3-bromopyridin-2-yl)carbamateHCID 178418339Butyllithium

Product 1

HCID 86690661Tert-butyl[3-(1-hydroxy-4-phenylcyclohexyl)pyridin-2-yl]carbamateYield 10.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (3-bromopyridin-2-yl)carbamate (4 g) in THF (dry) (20 mL) was added dropwise n-butyllithium (1.6 M in hexane) (20.1 mL) at −78° C. and the mixture was stirred at the same temperature under nitrogen for 1 hr to give a yellow suspension. A solution of 4-phenylcyclohexanone (3.06 g) in THF (dry) (30 mL) was added dropwise at −78° C. and the mixture was stirred at room temperature under nitrogen overnight. The mixture was quenched with water at 0° C. and extracted with EtOAc. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (560 mg) as a pale yellow solid.

Workup

  1. customto give a yellow suspension
  2. stirringthe mixture was stirred at room temperature under nitrogen overnight
  3. customThe mixture was quenched with water at 0° C.
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-464f8da631e846368986a89bd79737bf
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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