tert-Butyl N-(2-bromoethyl)carbamate → HCID 71003970, compound

HRID 2201754Notes

Reaction equation

HRID 2201754 reaction equation
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10](=[O:18])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>C(#N)C>[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:15]=2)[C:10](=[O:18])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 71003969HCID 71003969, compound

Product 1

HCID 71003970HCID 71003970, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-benzyl-5-hydroxyisoindolin-1-one (360 mg, 1.51 mmol), CsCO3 (980 mg, 3.01 mmol) and tert-butyl 2-bromoethylcarbamate (506 mg, 2.26 mmol) in 4 mL of acetonitrile was heated up to 80° C. for 4 hours, TLC showed complete conversion. The solvent was evaporated and the residue was dissolved in ethyl acetate, then water was added, this was separated. The organic phase was dried on Na2SO4 and the solvent was evaporated. The residue was purified by flash-chromatography on silica gel with 100% ethyl acetate, 426 mg (1.11 mmol, 74%) of the product was obtained.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. additionwater was added
  4. customthis was separated
  5. customThe organic phase was dried on Na2SO4
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash-chromatography on silica gel with 100% ethyl acetate

Sources & evidence

ORD record
ord-fb39a51ca5f84d31a08dca718676538e
Source dataset
uspto-grants-2016_06
Patent number
US09365512B2

Reaction notes

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