Lithium Bromide → cis-(4-Bromomethyl-cyclopent-2-enyl)-carbamic acid tert-butyl ester

HRID 1789898Notes

Reaction equation

HRID 1789898 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][C@H:12]([CH2:14]OS(C)(=O)=O)[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[Br-:21]>CC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:13][C@@H:12]([CH2:14][Br:21])[CH:11]=[CH:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 21109977HCID 21109977, compound

Product 1

HCID 69650185cis-(4-Bromomethyl-cyclopent-2-enyl)-carbamic acid tert-butyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of cis-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl ester (2.51 g, 8.6 mmol) and LiBr (2.24 g, 25.8 mmol) in dry acetone (20 mL) was refluxed overnight. The reaction mixture was allowed to cool to room temperature, filtered and concentrated. The residue was dissolved in CH2Cl2 and washed with water, dried and concentrated under reduced pressure to give of cis-(4bromomethyl-cyclopent-2-enyl)-carbamic acid tert-butyl ester (2.23 g, 94%).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-652ce7d0074a4fb2b3075afd82dbebc3
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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