Sulfuric Acid → 1-[(1,1-Dioxidoisothiazolidin-2-yl) methyl]tricyclo[3.3.1.03,7]nonan-3-amine

HRID 1015540Notes

Reaction equation

HRID 1015540 reaction equation
[O:1]=[S:2]1(=[O:20])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]12[CH2:16][CH:12]3[CH2:13][CH:14]([CH2:15]1)[C:10](C(O)=O)([CH2:11]3)[CH2:9]2.OS(O)(=O)=O.[N-:26]=[N+]=[N-].[Na+]>C(Cl)(Cl)Cl.O>[O:1]=[S:2]1(=[O:20])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]12[CH2:16][CH:12]3[CH2:13][CH:14]([CH2:15]1)[C:10]([NH2:26])([CH2:11]3)[CH2:9]2

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 673003471-[(1,1-Dioxidoisothiazolidin-2-yl)methyl]tricyclo[3.3.1.03,7]nonane-3-carboxylicacid

Product 1

HCID 670178751-[(1,1-Dioxidoisothiazolidin-2-yl) methyl]tricyclo[3.3.1.03,7]nonan-3-amineYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of the acid obtained in step III (0.39 g, 1.31 mmol) in CHCl3 (7 mL) was added conc. H2SO4 (1.4 mL, 26 mmol). Solid NaN3 (0.26 g, 3.93 mmol) was added slowly in portions by keeping the reaction temperature below 40° C. The reaction mixture was stirred at r.t for 2, h then it was cooled to ice bath temperature, diluted with water, and extracted with EtOAc. The aqueous layer was basified by adding 50% NaOH solution and extracted with CHCl3. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure to obtain 1-[(1,1-dioxidoisothiazolidin-2-yl) methyl]tricyclo[3.3.1.03,7]nonan-3-amine (0.26 g) as viscous liquid in 74% yield. m/z (M+1) 271; 1H NMR (CDCl3) 300 MHz δ 3.32 (t, J=6.8 Hz, 2H), 3.10 (t, J=7.4 Hz, 2H), 2.92 (s, 2H), 2.40-2.28 (m, 3H), 2.01-1.83 (m, 3H), 1.75-1.52 (m, 6H), 1.50-1.43 (m, 1H), 1.39-1.32 (m, 1H).

Workup

  1. customthe reaction temperature below 40° C
  2. temperatureit was cooled to ice bath temperature
  3. extractionextracted with EtOAc
  4. additionby adding 50% NaOH solution
  5. extractionextracted with CHCl3
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9da8352a591141a0833817df22dcd220
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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