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Chemical Structure| 28114-87-6 Chemical Structure| 28114-87-6

Structure of 28114-87-6

Chemical Structure| 28114-87-6

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Product Details of [ 28114-87-6 ]

CAS No. :28114-87-6
Formula : C8H12O2
M.W : 140.18
SMILES Code : O=C(C1CC2(CCC2)C1)O
MDL No. :MFCD19228416
InChI Key :FUQHLUSGMOSPRQ-UHFFFAOYSA-N
Pubchem ID :20320775

Safety of [ 28114-87-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 28114-87-6 ]

* 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.

  • Downstream synthetic route of [ 28114-87-6 ]

[ 28114-87-6 ] Synthesis Path-Downstream   1~33

  • 4
  • [ 64775-97-9 ]
  • [ 28114-87-6 ]
YieldReaction ConditionsOperation in experiment
92% With pyridine; at 115℃; A solution of spiro[3.3]heptane-2,2-dicarboxylic acid (1.737 g, 9.43 mmol) in pyridine (20 mL) was heated at 115 C. overnight, cooled to RT and concentrated to dryness. The residue was treated with 6M HCL, extracted with DCM (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford spiro[3.3]heptane-2-carboxylic acid (1.21 g, 92%). 1H NMR (400 MHz, DMSO-d6): delta 11.98 (s, 1H), 2.85 (m, 1H), 2.15-2.03 (m, 4H), 1.96 (t, J=7.3 Hz, 2H), 1.84 (t, J=7.3 Hz, 2H), 1.76-1.70 (m, 2H).
  • 9
  • [ 28114-87-6 ]
  • t-butyl spiro<3.3>heptane-3-peroxycarboxylate [ No CAS ]
  • 10
  • [ 28114-87-6 ]
  • [ 3617-81-0 ]
  • 11
  • [ 28114-87-6 ]
  • [ 3617-80-9 ]
  • 12
  • [ 28114-87-6 ]
  • [ 3617-83-2 ]
  • 13
  • [ 28114-87-6 ]
  • [ 3617-84-3 ]
  • 14
  • [ 64775-96-8 ]
  • [ 28114-87-6 ]
  • 16
  • [ 28114-87-6 ]
  • [ 74-88-4 ]
  • [ 64776-06-3 ]
YieldReaction ConditionsOperation in experiment
82.5% With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; sodium hydroxide; A. Preparation of 2-Methyl<strong>[28114-87-6]spiro[3.3]heptane-2-carboxylic acid</strong> A slurry of 2.15 g (44.2 mmol) of sodium hydride (50% in oil) in 45.0 ml of dry THF was stirred under argon at -20 C. A solution of 5.52 g (40.0 mmol) of <strong>[28114-87-6]spiro[3.3]heptane-2-carboxylic acid</strong> in 5.0 ml of dry THF was added dropwise. The reaction mixture was stirred for 0.5 hr at -20 C. A solution of 44.5 mmol of freshly-prepared, -20 C lithium diisopropylamide in 31.0 ml of THF was added to the reaction mixture. The reaction mixture was stirred for 0.3 hr at 0 C. Methyl iodide (2.80 ml, 44.5 mmol) was added, and the reaction mixture stirred an additional 2.0 hr at 25 C. The reaction mixture was cooled to -20 C and the reaction quenched by careful addition of cold 10% aqueous HCl. The mixture was extracted with 1:1 ethylacetate-ether. The extracts were washed with brine, then dried (MgSO4), filtered, and solvents evaporated in vacuo. The residue was dissolved in 1 N NaOH and extacted three times with ether. The aqueous layer was acidified with 6 N HCl and extracted with 1:1 ethyl-acetate-ether. These extracts were washed with brine, dried (MgSO4), filtered and evaporated in vacuo to yield 5.1 g of 2-methyl<strong>[28114-87-6]spiro[3.3]heptane-2-carboxylic acid</strong> as a light yellow oil (82.5%). Analysis -- NMR (CHCl3): delta1.35, singlet, 3H; 11.4, broad singlet, 1H.
  • 17
  • spiro[3.3]heptane-3,3-dicarboxylic acid [ No CAS ]
  • [ 28114-87-6 ]
YieldReaction ConditionsOperation in experiment
E. Preparation of Spiro[3.3]heptane-2-carboxylic acid Crude spiro[3.3]heptane-3,3-dicarboxylic acid (8.3 g, 0.046 mole) was thermally decarboxylated by heating the material at 220 C for 30 min. Heating was discontinued when the evolution of carbon dioxide ceased. The mixture was cooled to yield 5.38 g of spiro[3.3]heptane-2-carboxylic acid. Analysis -- NMR(CDCl3): delta1.5-2.3, multiplet, 11H; 11.0 ppm, broad singlet, 1H.
  • 18
  • diisopropyl spiro[3.3]heptane-2,2-dicarboxylate [ No CAS ]
  • [ 28114-87-6 ]
  • 19
  • [ 3779-29-1 ]
  • [ 28114-87-6 ]
  • 20
  • [ 4415-73-0 ]
  • [ 28114-87-6 ]
  • 21
  • [ 28114-87-6 ]
  • spiro[3.3]heptane-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% A solution of <strong>[28114-87-6]spiro[3.3]heptane-2-carboxylic acid</strong> (0.5 g, 3.57 mmol) in DCM (5 mL) was treated with oxalyl chloride (0.406 mL, 4.64 mmol) and 1 drop of DMF and stirred at RT for 2 h. The mixture was added drop-wise to a mixture of NH4OH (5 mL, 128 mmol) and THF (5 mL) and stirred at RT overnight. The mixture was treated with H2O, the solids removed via filtration, the filtrate saturated with solid NaCl, extracted with 3:1 DCM/THF (3×) and the combined organics were washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to dryness to afford spiro[3.3]heptane-2-carboxamide (440 mg, 89%). 1H NMR (400 MHz, DMSO-d6): delta 7.07 (s, 1H), 6.62 (s, 1H), 2.76 (m, 1H), 2.01 (m, 4H), 1.96 (t, J=7.2 Hz, 2H), 1.80 (m, 2H), 1.76-1.69 (m, 2H).
  • 22
  • [ 28114-87-6 ]
  • N-((5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)spiro[3.3]heptane-2-carboxamide [ No CAS ]
  • 23
  • [ 28114-87-6 ]
  • N-((6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)spiro[3.3]heptane-2-carboxamide [ No CAS ]
  • 24
  • [ 28114-87-6 ]
  • [ 75-65-0 ]
  • tert-butyl spiro[3.3]heptan-2-ylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Compound 4 (1.70 g, 12.13 mmol) and triethylamine (1.47 g, 14.56 mmol) were dissolved in toluene (50 mL), and then DPPA (3.66 g, 13.34 mmol) was added. The reaction mixture was slowly heated to 100 C (oil bath), and the mixture was stirred for 15 min. Then t-BuOH (8.98 g, 121.3 mmol) was added, and the resulting mixture was stirred overnight at the same temperature. The reaction mixture was cooled, poured into EtOAc (50 mL), and washed with aq NaHCO3. The organic phase was dried over Na2SO4, filtered, and evaporated. The crude product was purified by column chromatography (hexane: EtOAc=10: 1) and recrystallized from hexane-EtOAc mixture. The yield was 1.79 g (8.47 mmol 70%). Colorless needles. Mp 104-105 C. TLC: Rf=0.47 (hexane: EtOAc=10: 1). 1H NMR (400 MHz, CDCl3), delta: 4.73 (s, 1H), 4.06-3.71 (m, 1H), 2.42-2.26 (m, 2H), 1.97 (t, J=7.0 Hz, 2H), 1.86 (t, J=6.7 Hz, 2H), 1.81-1.65 (m, 4H), 1.39 (s, 9H). 13C NMR (101 MHz, CDCl3), delta: 154.93, 78.93, 43.50, 41.25, 37.04, 34.68, 34.05, 28.35, 16.68. MS (GC-MS) 155 (M+-C4H8), 110 (M+-Boc). HRMS calcd for C12H22O2N+212.1645, found 212.1643.
  • 25
  • [ 28114-87-6 ]
  • spiro[3.3]heptan-2-amine hydrochloride [ No CAS ]
  • 26
  • [ 28114-87-6 ]
  • 2-(spiro[3.3]heptan-2-yl)propan-2-ol [ No CAS ]
  • 27
  • [ 28114-87-6 ]
  • 2-(2-azidopropan-2-yl)spiro[3.3]heptane [ No CAS ]
  • 28
  • [ 28114-87-6 ]
  • 2-(spiro[3.3]heptan-2-yl)propan-2-amine [ No CAS ]
  • 29
  • [ 28114-87-6 ]
  • [ 64-17-5 ]
  • ethyl spiro[3.3]heptane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With sulfuric acid; at 0℃; for 20.0h;Reflux; Concentrated H2SO4 (0.5 mL) was added dropwise to a solution of spiro[3.3jheptane-2-carboxylic acid (1 g, 7.14 mmol) in EtOH (30 mL) at 0 C and the reactionmixture was refluxed for 20 h. After completion of the reaction, the solvent was removed and the reaction mixture was dissolved in EtOAc (150 mL). The organic layer was washed with saturated NaHCO3 solution (100 mL), dried over anhydrous MgSO4, and filtered. The filtrate was concentrated in vacuo to give ethyl spiro[3.3jheptane-2-carboxylate (1.2 g, 100%) as a colorless oil which was used directly in the next step. ?H NMR (500 MHz, CDC13) oe 4.04 (q, J= 7.0 Hz, 2H), 2.94-2.78 (m, 1H), 2.14 (p, J 11.0 Hz, 4H), 1.95 (t, J= 7.5 Hz, 2H), 1.85 (t, J = 7.4 Hz, 2H), 1.73 (dd, J 15.0 Hz, 7.5 Hz, 2H), 1.17 (t, J= 7.5 Hz, 3H).
100% With sulfuric acid; at 0℃; for 20.0h;Reflux; Concentrated H2S04 (0.5 mL) was added dropwise to a solution ofspiro[3.3jheptane-2-carboxylic acid (1 g, 7.14 mmol) in EtOH (30 mL) at 0 C and the reaction mixture was refluxed for 20 h. After completion of the reaction, the solvent was removed and the reaction mixture was dissolved in EtOAc (150 mL). The organic layer was washed with saturated NaHCO3 solution (100 mL), dried over anhydrous MgSO4, and filtered. The filtrate was concentrated in vacuo to give ethyl spiro[3.3jheptane-2-carboxylate (1.2 g, 100%) as acolorless oil which was used directly in the next step. ?H NMR (500 MHz, CDC13) oe 4.04 (q, J = 7.0 Hz, 2H), 2.94-2.78 (m, 1H), 2.14 (p, J 11.0 Hz, 4H), 1.95 (t, J= 7.5 Hz, 2H), 1.85 (t, J = 7.4 Hz, 2H), 1.73 (dd, J 15.0 Hz, 7.5 Hz, 2H), 1.17 (t, J= 7.5 Hz, 3H).
With sulfuric acid; at 0℃; for 20.0h;Reflux; 2-(Spiro[3.3]heptan-2-yl)propan-2-amine (0357) [00233] Concentrated H2SO4 (0.5 mL) was added dropwise to a solution of (0358) <strong>[28114-87-6]spiro[3.3]heptane-2-carboxylic acid</strong> (1 g, 7.14 mmol) in EtOH (30 mL) at 0 C and the reaction mixture was refluxed for 20 h. After completion of the reaction, the solvent was removed and the reaction mixture was dissolved in EtOAc (150 mL). The organic layer was washed with saturated NaHCO3 solution (100 mL), dried over anhydrous MgSO4, and filtered. The filtrate was concentrated in vacuo to give ethyl spiro[3.3]heptane-2-carboxylate (1.2 g, 100%) as a colorless oil which was used directly in the next step. 1H NMR (500 MHz, CDCl3) delta 4.04 (q, J = 7.0 Hz, 2H), 2.94-2.78 (m, 1H), 2.14 (p, J = 11.0 Hz, 4H), 1.95 (t, J = 7.5 Hz, 2H), 1.85 (t, J = 7.4 Hz, 2H), 1.73 (dd, J = 15.0 Hz, 7.5 Hz, 2H), 1.17 (t, J = 7.5 Hz, 3H).
  • 30
  • [ 28114-87-6 ]
  • [ 182876-24-0 ]
  • dispiro[3.1.3.1]decan-2-ylmethyl spiro[3.3]heptane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
56.3% With toluene-4-sulfonic acid; In tetrahydrofuran; benzene; for 4.0h;Dean-Stark; Heating; 225 mg (1.6 mmol) of spiro [3,3] heptane-2-carboxylic acid and 500 mg (1.9 mmol) ofIsopyro [3,1,3,1] decan-2-ylmethanolAnd314 mg (1.6 mmol) of para-toluenesulfonic acid was dissolved in 7 ml of benzene solution and 3 ml of tetrahydrofuran solution, followed by stirring at 80 C with a Dean-Stark trap.After 4 hours, the organic material was extracted with 15 ml of distilled water and 15 ml of ethyl ether. The organic extracts were dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. 254 mg (0.9 mmol, spiro [3,3] heptane-2-carboxylic acid : 56.3%) of the compound represented by the formula (11) was obtained.
  • 31
  • [ 28114-87-6 ]
  • [ 4415-82-1 ]
  • cyclobutylmethyl spiro[3.3]heptane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.8% With toluene-4-sulfonic acid; In tetrahydrofuran; benzene; for 4.0h;Dean-Stark; Heating; 1.40 g (9.6 mmol) of Spiro [3,3] heptane-2-carboxylic acid and 1.00 g (11.50 mmol) of Cyclobutylmethanol and 1.88 g (9.6 mmol) ofParatoluenesulfonic acid was dissolved in 12 ml of benzene solution and 4 ml of tetrahydrofuran solution, and then a Dean-Stark trap was provided and stirred at 80 C. After 4 hours, the organic material was extracted with 15 ml of distilled water and 15 ml of ethyl ether. The organic extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (hexane: ethyl acetate = 50: 1) to obtain 1.4 g (6.7 mmol, spiro [3,3] heptane- : 69.8%) of the compound represented by the formula (8) was obtained.
  • 32
  • [ 28114-87-6 ]
  • [ 4483-67-4 ]
  • spiro[3.3]heptan-2-ylmethyl spiro[3.3]heptane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.5% With toluene-4-sulfonic acid; In tetrahydrofuran; benzene; for 4.0h;Dean-Stark; Heating; The reaction formula of Example 4 can be represented as shown in Formula 17 below.467 mg (3.3 mmol) of Spiro [3,3] heptane-2-carboxylic acid and 500 mg (3.9 mmol) of Spiro [3,3] hept-2-ylmethanolAnd647 mg (3.3 mmol) of Paratoluenesulfonic acid was dissolved in 7 ml of a benzene solution and 3 ml of tetrahydrofuran solution, and then a Dean-Stark trap was provided and stirred at 80 C.After 4 hours, the organic material was extracted with 15 ml of distilled water and 15 ml of ethyl ether. The organic extracts were dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. 670 mg (2.7 mmol, spiro [3,3] heptane-2-carboxylic acid : 81.8%) of the compound represented by the formula (10) was obtained.
  • 33
  • [ 28114-87-6 ]
  • [ 100-46-9 ]
  • N-benzylspiro[3.3]heptane-2-carboxamide [ No CAS ]
 

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