Acetic Acid → 1-(1,1-Dioxido iso thiazolidin-2-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid

HRID 1015526Notes

Reaction equation

HRID 1015526 reaction equation
[OH-].[Na+].BrBr.Br[O-].[O:7]=[S:8]1(=[O:25])[CH2:12][CH2:11][CH2:10][N:9]1[C:13]12[CH2:21][CH:17]3[CH2:18][CH:19]([CH2:20]1)[C:15]([C:22](=[O:24])C)([CH2:16]3)[CH2:14]2.CC(O)=[O:28]>O1CCOCC1.O>[O:7]=[S:8]1(=[O:25])[CH2:12][CH2:11][CH2:10][N:9]1[C:13]12[CH2:21][CH:17]3[CH2:18][CH:19]([CH2:20]1)[C:15]([C:22]([OH:28])=[O:24])([CH2:16]3)[CH2:14]2

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 5460626HypobromiteHCID 866427401-[1-(1,1-Di oxido isothiazolidin-2-yl)tricyclo[3.3.1.03,7]non-3-yl]ethanone

Product 1

HCID 866427391-(1,1-Dioxido iso thiazolidin-2-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acidYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred mixture of NaOH (2.1 g, 53.0 mmol), H2O (14 mL), and 1,4 dioxane (4 mL) at ice bath temperature was added Br2 (1.0 mL, 19.8 mmol) and the mixture was stirred for 5 minutes. Thus formed hypobromite solution was added drop-wise to a stirred solution of the compound obtained in step I (1.0 g, 3.53 mmol) in 1,4-dioxane (7 mL) at 10° C. The temperature of the reaction was gradually brought to room temperature and the reaction was stirred for 1 h, then it was cooled to ice bath temperature and quenched by adding AcOH (3.9 mL, 65.7 mmol). The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-(1,1-dioxido iso thiazolidin-2-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid as a viscous liquid (0.9 g) in 90% yield. m/z (M+1) 286; 1H NMR (CDCl3) 300 MHz δ 3.37 (t, J=6.6 Hz, 2H), 3.16 (t, J=7.8 Hz, 2H), 2.84-2.76 (m, 1H), 2.52-2.41 (m, 2H), 2.38-2.26 (m, 2H), 2.25-1.98 (m, 6H), 1.85-1.72 (m, 2H), 1.61 (dd, J=2.2, 11.3 Hz, 1H).

Workup

  1. customwas gradually brought to room temperature
  2. stirringthe reaction was stirred for 1 h
  3. temperatureit was cooled to ice bath temperature
  4. customquenched
  5. extractionextracted with EtOAc
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b3156695f7394d3da2fdbaedfa143a93
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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