Hydrochloric Acid → 3-[(S)-1-(4-Bromo-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

HRID 1615120Notes

Reaction equation

HRID 1615120 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C:13]3([CH2:27][CH2:26][C:18]4(OCC(C)(C)C[O:19]4)[CH2:17][CH2:16]3)[O:12][C:11]2=[O:28])[CH3:9])=[CH:4][CH:3]=1.Cl>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C:13]3([CH2:27][CH2:26][C:18](=[O:19])[CH2:17][CH2:16]3)[O:12][C:11]2=[O:28])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 679959573-[(S)-1-(4-bromo-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one

Product 1

HCID 565957523-[(S)-1-(4-Bromo-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-[(S)-1-(4-bromo-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one (0.75 g), aqueous hydrochloric acid (5 mL), and acetone (10 mL) is stirred at room temperature overnight. The acetone is then evaporated, and the residue is diluted with saturated aqueous K2CO3 solution and extracted with ethyl acetate. The combined extracts are washed with water and brine, dried (MgSO4), and concentrated to give the crude title compound that is used without further purification. Yield: 0.70 g (ca. 65% pure); Mass spectrum (ESI+): m/z=366/368 (Br) [M+H]+.

Workup

  1. customThe acetone is then evaporated
  2. additionthe residue is diluted with saturated aqueous K2CO3 solution
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts are washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed3af4e887a147b5a88b0efb041aad39
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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