Cesium carbonate → HCID 86709751, compound

HRID 1400250Notes

Reaction equation

HRID 1400250 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][C:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:23])[CH3:22].CCCCCC.C(OCC)(=O)C>C(#N)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH2:23][C:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:20])[CH3:22]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 124591-Chloro-2-naphthol2×HCID 21226206Ethyl acetate hexaneHCID 74788455Carbamic acid, N-(2-bromo-1,1-dimethylethyl)-, 1,1-dimethylethyl ester

Product 1

HCID 86709751HCID 86709751, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-chloronaphthalen-2-ol (1.5 mmol) and Cs2CO3 (3 mmol) in acetonitrile was added tert-butyl (1-bromo-2-methylpropan-2-yl)carbamate (3 mmol). The resulting mixture was heated at reflux overnight. After TLC control (n-hexane/ethyl acetate 7:3) showed the disappearance of 1-chloronaphthalen-2-ol, solvent was evaporated in vacuo and the residue was dissolved in 15 mL of ethyl acetate and washed with water (3×5 mL), brine (10 mL) and dried over Na2SO4. The evaporation of solvent afforded tert-butyl {1-[(1-chloronaphthalen-2-yl)oxy]-2-methylpropan-2-yl}carbamate as a pale oil (51% yield) which was dissolved in 5 mL of 4 M HCl solution in dioxane. The resulting mixture was stirred at room temperature for 18 h. After HPLC-MS control, the solvent was distilled off and the residue was dissolved in dichloromethane and wash 2 times with NaOH 1N to afford 1-[(1-chloronaphthalen-2-yl)oxy]-2-methylpropan-2-amine as a pale oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customwas evaporated in vacuo
  4. dissolutionthe residue was dissolved in 15 mL of ethyl acetate
  5. washwashed with water (3×5 mL), brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. customThe evaporation of solvent

Sources & evidence

ORD record
ord-b1fcb02dc3a649d1907bfac3f2fd8edb
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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