4-Bromo-2-cyclopentyl-5-nitrophenyl methyl carbonate → HCID 59394974, compound

HRID 1465077Notes

Reaction equation

HRID 1465077 reaction equation
[C:1](=[O:20])([O:18][CH3:19])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([Br:12])=[CH:5][C:4]=1[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C(O)(=O)C.O.C(#N)C.CO.[Zn]>[C:1](=[O:20])([O:18][CH3:19])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([Br:12])=[CH:5][C:4]=1[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 1

HCID 593949534-Bromo-2-cyclopentyl-5-nitrophenyl methyl carbonate

Product 1

HCID 59394974HCID 59394974, compoundYield 98.6%

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

4-bromo-2-cyclopentyl-5-nitrophenyl methyl carbonate (211 mg, 0.61 mmol) was dissolved in a mixture of glacial acetic acid (3 mL) and water (1 mL). Additional acetic acid (1 mL) was added to facilitate stirring. Zn dust (401 mg, 6.13 mmol) was added at room temperature and the reaction stirred for 10 min. The reaction was diluted with acetonitrile (5 mL) and methanol (5 mL) and filtered. The solution was diluted with ethyl acetate, washed with 50% saturated aqueous NaHCO3 (2×20 mL) and brine, dried over Na2SO4, filtered, and dried down to provide 5-amino-4-bromo-2-cyclopentylphenyl methyl carbonate as a light orange solid (189 mg, 98% yield). LC/MS m/z 315.0 [M+H]+.

Workup

  1. stirringthe reaction stirred for 10 min
  2. filtrationfiltered
  3. additionThe solution was diluted with ethyl acetate
  4. washwashed with 50% saturated aqueous NaHCO3 (2×20 mL) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customdried down

Sources & evidence

ORD record
ord-a1e94bf4edf14f00be6e00aeaa99aeab
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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