Sodium Bicarbonate → 2-(4-Bromophenyl)-5,8-dioxaspiro[3.4]octan-2-amine

HRID 222001Notes

Reaction equation

HRID 222001 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:16]C(=O)OC(C)(C)C)[CH2:11][C:10]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:9]2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH2:16])[CH2:11][C:10]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59161518tert-Butyl (2-(4-bromophenyl)-5,8-dioxaspiro[3.4]octan-2-yl)carbamate

Product 1

HCID 582166022-(4-Bromophenyl)-5,8-dioxaspiro[3.4]octan-2-amine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl [2-(4-bromophenyl)-5,8-dioxaspiro[3.4]oct-2-yl]carbamate (1-5) (3.7 g, 9.63 mmol) in TFA (20 mL) was stirred at room temperature for 1 hour. The mixture was poured into a sat. NaHCO3 solution, extracted with CHCl3, dried (Na2SO4), filtered, and concentrated under reduced pressure to give 2-(4-bromophenyl)-5,8-dioxaspiro[3.4]octan-2-amine (7-1).

Workup

  1. extractionextracted with CHCl3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bcf5fcd803f549af8344fb6eeee91c42
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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