Bromine → 1-Acetamido-4-bromo-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

HRID 863522Notes

Reaction equation

HRID 863522 reaction equation
[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].O.O.O.C([O-])(=O)C.[Na+].[Br:28]Br>C(O)(=O)C>[C:1]([NH:4][C:5]1[C:14]2[CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:11][CH2:10][C:9]=2[C:8]([Br:28])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 196962461-Acetamido-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthaleneHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 196962081-Acetamido-4-bromo-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-acetamido-7-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalene (0.36 g, 1.4 mmol) and sodium acetate trihydrate (0.38 g, 2.8 mmol) in acetic acid (15 mL) was treated with bromine (0.27 g, 1.7 mmol) and stirred at room temperature for 2 h. A precipitate was collected by filtration and the filtrate evaporated. The two solids were combined and dissolved in methylene chloride; water. The mixture was basified with 12.5% NaOH, and the organic phase separated. The aqueous layer was back extracted and the combined organic layers were dried over sodium sulfate, filtered and evaporated. The residue was heated in diethyl ether to form a solid, which was collected and dried (0.31 g).

Workup

  1. filtrationA precipitate was collected by filtration
  2. customthe filtrate evaporated
  3. dissolutiondissolved in methylene chloride
  4. customthe organic phase separated
  5. extractionThe aqueous layer was back extracted
  6. dry with materialthe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. temperatureThe residue was heated in diethyl ether
  10. customto form a solid, which
  11. customwas collected
  12. customdried (0.31 g)

Sources & evidence

ORD record
ord-6a6d7991919f49c697e7ed58b5f3c16f
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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