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Chemical Structure| 107869-45-4 Chemical Structure| 107869-45-4
Chemical Structure| 107869-45-4

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(3aR,6S)-8,8-Dimethyl-4,5,6,7-tetrahydro-3H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide

CAS No.: 107869-45-4

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Cat. No.: A175160 Purity: 98%

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Product Details of [ 107869-45-4 ]

CAS No. :107869-45-4
Formula : C10H15NO2S
M.W : 213.30
SMILES Code : CC1(C)[C@](C2)(CC[C@@]1([H])C3)C3=NS2(=O)=O
MDL No. :MFCD00064576

Safety of [ 107869-45-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis [ 107869-45-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 107869-45-4 ]
  • Downstream synthetic route of [ 107869-45-4 ]

[ 107869-45-4 ] Synthesis Path-Upstream   1~4

  • 1
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YieldReaction ConditionsOperation in experiment
92% With Amberlyst H+ resin In toluene for 4 h; Heating / reflux EXAMPLE 1; (1R)-(+)-2,10-Camphor Sultam (Scheme 3, 3-1); To a solution of (-) camphor sulfonic acid (1.45 kg, 6.25 mol) in chloroform (7 L) under reflux condition is added thionyl chloride (0.896 kg, 7.5 mol) over a period of 1 h. The reaction mixture is refluxed for 16 h and then cooled to 4° C. using an ice bath. This cooled reaction mixture is added slowly to conc. NH4OH (15 L) while maintaining the temperature below 15° C. during the addition. After addition, the mixture is stirred for 4 h at room temperature. The organic layer is separated and the aqueous layer is extracted with chloroform (2.x.2 L). The combined organic extracts are washed with brine (4 L) and dried over MgSO4. After filtration, the filtrate is concentrated under vacuum and dried to give 1.2 kg (83percent) of camphor sulfonamide. In one experiment at 145 g scale of camphor sulfonic acid, the use of dichloromethane instead of chloroform for the reaction and extraction gives comparable yields. To a suspension of the camphor sulfonamide (1.2 kg, 5.2 mol) in toluene (15 L) is added Amberlyst H+ resin (150 g), and the mixture is heated at reflux for 4 h with the water formed removed azeotropically using a Dean-Stark water separator. The reaction mixture is filtered hot to remove the resin. The filtrate on cooling gave a white solid which is collected by filtration to give 1.02 kg (92percent) of the desired imine. To the above imine (100 g, 0.47 mol) in ethanol (0.75 L) is added Raney Nickel (100 g) and the mixture is hydrogenated at 40 psi for 2 h. The catalyst is removed by filtration and the filtrate concentrated under vacuum to give the product 3-1 as a white solid
References: [1] Tetrahedron, 1986, vol. 42, # 14, p. 4035 - 4044.
[2] Chemical Communications, 1998, # 15, p. 1549 - 1550.
[3] Journal of the American Chemical Society, 1988, vol. 110, p. 8477.
[4] Patent: US2006/128789, 2006, A1, . Location in patent: Page/Page column 7.
[5] Organic Process Research and Development, 2005, vol. 9, # 2, p. 193 - 197.
[6] Organic Syntheses, 1990, vol. 69, p. 158 - 158.
  • 2
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YieldReaction ConditionsOperation in experiment
32 mg With NADP In aq. phosphate buffer at 20℃; Enzymatic reaction To isolate compounds 17, a large scale reaction (250 mE) was set up with P450 mutant III-H2 (2 tM) in 50 mM phosphate buffer (pH 8.0) in the presence of (+)-10,2- camphorsultam (54 mg, final conc.: 1 mM), PTDH at 2 tM, NADP at 150 tM, and sodium phosphite at 50 mM. The mixture was stirred overnight at room temperature. After removal of the enzyme through filtration, the filtrate was loaded on a Cl 8 resin column and the hydroxylated products eluted with acetonitrile. The eluate was dried with Na2504, concentrated in vacuum, and purified by flash chromatography (gradient from 10 to 40percent ethyl acetate in hexanes) to afford 17 (32 mg). Compound 17 (camphorsulfonimine). ‘H NMR (500 MHz, CDC13): ö=0.92 (s, 3 H), 1.13 (s, 3 H), 1.50 (m,1H),1.83(m,1H),2.07-2.15(m,2H),2.30(m,1H),2.43 (d, 1 H, J=18.8 Hz), 2.82 (m, 1 H), 3.02 (d, 1 H, J=13.2 Hz), 3.23 (d, 1 H, J=13.2 Hz); ‘3C NMR (100 MHz, CDC13):ö=18.9, 19.4, 26.6, 28.3, 35.9, 44.5, 47.9, 49.4, 64.5, 195.1; MS (ESI) calcd for C,QH,6N025 [M+H]/z: 214.09. found:214.42.
References: [1] Patent: US9273342, 2016, B2, . Location in patent: Page/Page column 45.
  • 3
  • [ 35963-20-3 ]
  • [ 107869-45-4 ]
References: [1] Organic Letters, 2000, vol. 2, # 26, p. 4157 - 4160.
[2] Journal of the American Chemical Society, 1988, vol. 110, p. 8477.
[3] Tetrahedron, 1986, vol. 42, # 14, p. 4035 - 4044.
[4] Organic Process Research and Development, 2005, vol. 9, # 2, p. 193 - 197.
[5] Organic Syntheses, 1990, vol. 69, p. 158 - 158.
  • 4
  • [ 21286-54-4 ]
  • [ 107869-45-4 ]
References: [1] Organic Letters, 2000, vol. 2, # 26, p. 4157 - 4160.
[2] Chemical Communications, 1998, # 15, p. 1549 - 1550.
[3] Tetrahedron, 1986, vol. 42, # 14, p. 4035 - 4044.
[4] Organic Process Research and Development, 2005, vol. 9, # 2, p. 193 - 197.
[5] Organic Syntheses, 1990, vol. 69, p. 158 - 158.
 

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