Home Cart 0 Sign in  

[ CAS No. 152533-47-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 152533-47-6
Chemical Structure| 152533-47-6
Structure of 152533-47-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 152533-47-6 ]

Related Doc. of [ 152533-47-6 ]

Alternatived Products of [ 152533-47-6 ]

Product Details of [ 152533-47-6 ]

CAS No. :152533-47-6 MDL No. :MFCD18633018
Formula : C11H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 211.26 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 152533-47-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.82
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.49
TPSA : 46.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : 1.25
Log Po/w (WLOGP) : 1.35
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : 1.01
Consensus Log Po/w : 1.42

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.74
Solubility : 3.85 mg/ml ; 0.0182 mol/l
Class : Very soluble
Log S (Ali) : -1.83
Solubility : 3.15 mg/ml ; 0.0149 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.21
Solubility : 13.0 mg/ml ; 0.0615 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.58

Safety of [ 152533-47-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 152533-47-6 ]

* 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 [ 152533-47-6 ]

[ 152533-47-6 ] Synthesis Path-Downstream   1~96

  • 1
  • [ 69045-79-0 ]
  • [ 152533-47-6 ]
  • (+/-)-endo-2-(2-Chloro-5-pyridinyl)-7-<(1,1-dimethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol [ No CAS ]
  • 2
  • [ 152533-47-6 ]
  • (2-endo)-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester [ No CAS ]
  • 3
  • (2-endo)-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester [ No CAS ]
  • [ 152533-47-6 ]
  • 4
  • (2-endo)-2-hydroxy-7-azabicyclo[2.2.1]heptanes-7-carboxylic acid tert-butyl ester [ No CAS ]
  • [ 152533-47-6 ]
  • 5
  • [ 910332-68-2 ]
  • [ 152533-47-6 ]
  • 8
  • [ 152533-47-6 ]
  • [ 510748-11-5 ]
  • 2-{4-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-ethyl]-6-methoxy-pyridin-3-yl}-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 9
  • [ 152533-47-6 ]
  • [ 510748-42-2 ]
  • 2-{2-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-ethyl]-6-methoxy-pyridin-3-yl}-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 10
  • [ 510748-36-4 ]
  • [ 152533-47-6 ]
  • 11
  • [ 152533-47-6 ]
  • [ 249291-79-0 ]
  • (1R,2S,4S)-2-(6-Chloro-2-methyl-pyridin-3-yl)-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester [ No CAS ]
  • 12
  • [ 152533-47-6 ]
  • [ 550347-54-1 ]
  • (1R,2S,4S)-2-(6-Chloro-4-methyl-pyridin-3-yl)-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester [ No CAS ]
  • 13
  • [ 152533-47-6 ]
  • C13H15ClN2 [ No CAS ]
  • 14
  • [ 152533-47-6 ]
  • C13H15ClN2 [ No CAS ]
  • 15
  • [ 152533-47-6 ]
  • C13H15ClN2 [ No CAS ]
  • 16
  • [ 152533-47-6 ]
  • C13H15ClN2 [ No CAS ]
  • 17
  • [ 152533-47-6 ]
  • C14H18N2O [ No CAS ]
  • 18
  • [ 152533-47-6 ]
  • C14H18N2O [ No CAS ]
  • 19
  • [ 152533-47-6 ]
  • C14H18N2O [ No CAS ]
  • 20
  • [ 152533-47-6 ]
  • C14H18N2O [ No CAS ]
  • 21
  • [ 152533-47-6 ]
  • [ 510748-17-1 ]
  • 22
  • [ 152533-47-6 ]
  • [ 510748-50-2 ]
  • 23
  • [ 152533-47-6 ]
  • [ 510748-48-8 ]
  • 24
  • [ 152533-47-6 ]
  • [ 510748-15-9 ]
  • 25
  • [ 152533-47-6 ]
  • C19H26N2O3 [ No CAS ]
  • 26
  • [ 152533-47-6 ]
  • C19H26N2O3 [ No CAS ]
  • 27
  • [ 152533-47-6 ]
  • C16H17F3N2O2 [ No CAS ]
  • 28
  • [ 152533-47-6 ]
  • C15H14ClF3N2O [ No CAS ]
  • 29
  • [ 152533-47-6 ]
  • C19H26N2O3 [ No CAS ]
  • 30
  • [ 152533-47-6 ]
  • C16H17F3N2O2 [ No CAS ]
  • 31
  • [ 152533-47-6 ]
  • C15H14ClF3N2O [ No CAS ]
  • 32
  • [ 152533-47-6 ]
  • C19H26N2O3 [ No CAS ]
  • 33
  • [ 152533-47-6 ]
  • C15H14ClF3N2O [ No CAS ]
  • 34
  • [ 152533-47-6 ]
  • C16H17F3N2O2 [ No CAS ]
  • 35
  • [ 152533-47-6 ]
  • C15H14ClF3N2O [ No CAS ]
  • 36
  • [ 152533-47-6 ]
  • C16H17F3N2O2 [ No CAS ]
  • 37
  • [ 152533-47-6 ]
  • [ 510748-46-6 ]
  • 38
  • [ 152533-47-6 ]
  • [ 510748-13-7 ]
  • 39
  • [ 192118-47-1 ]
  • [ 152533-47-6 ]
  • 40
  • [ 152533-47-6 ]
  • [ 351019-20-0 ]
  • 41
  • [ 152533-47-6 ]
  • 7-tert-butoxycarbonyl-2-endo-[(2'-fluoro-5'-pyridinyl)]-7-azabicyclo[2.2.1]heptane [ No CAS ]
  • 43
  • [ 227454-54-8 ]
  • [ 152533-47-6 ]
  • 44
  • [ 227454-53-7 ]
  • [ 152533-47-6 ]
  • 46
  • [ 152533-47-6 ]
  • (+/-)-endo-2-(2-Chloro-5-pyridinyl)-7-<(1,1-dimethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptane [ No CAS ]
  • 48
  • [ 181873-33-6 ]
  • [ 152533-47-6 ]
  • 49
  • 3-oxo-7-aza-bicyclo[2.2.1]hept-5-ene-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester [ No CAS ]
  • [ 152533-47-6 ]
  • 51
  • [ 78293-47-7 ]
  • [ 152533-47-6 ]
  • 52
  • [ 152533-47-6 ]
  • (1R,2R,4S)-7-Benzyl-7-aza-bicyclo[2.2.1]heptan-2-ol [ No CAS ]
  • 53
  • [ 152533-47-6 ]
  • O-<(+/-)-endo-2-(2-Chloro-5-pyridinyl)-7-<(1,1-dimethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-yl> S-methyl xanthate [ No CAS ]
  • 54
  • [ 152533-47-6 ]
  • [ 140111-52-0 ]
  • 55
  • [ 152533-47-6 ]
  • 3-(2-Chloro-5-pyridinyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrole [ No CAS ]
  • 56
  • [ 152533-47-6 ]
  • (1S,2S,4R)-7-Aza-bicyclo[2.2.1]heptan-2-ol; compound with trifluoro-acetic acid [ No CAS ]
  • 57
  • [ 152533-47-6 ]
  • (1R,2S,4S)-2-(6-Chloro-pyridin-3-yl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester [ No CAS ]
  • 58
  • [ 152533-47-6 ]
  • N-Boc-(-)-epibatidine [ No CAS ]
  • 59
  • [ 152533-47-6 ]
  • (+/-)-2-(2-Chloro-5-pyridinyl)-7-<(1,1-dimethylethoxy)carbonyl>-7-azabicyclo<2.2.1>hept-2-ene [ No CAS ]
  • 60
  • [ 152533-42-1 ]
  • [ 152533-47-6 ]
  • 61
  • (+/-)-cis-1,2-Epoxy-4-<N-(phenylmethyl)amino>cyclohexane [ No CAS ]
  • [ 152533-47-6 ]
  • 62
  • (+/-)-cis-1,2-Epoxy-4-<N-(phenylmethyl)-N-(trifluoroacetyl)amino>cyclohexane [ No CAS ]
  • [ 152533-47-6 ]
  • 63
  • (1S,2R,4R)-7-Aza-bicyclo[2.2.1]heptan-2-ol; hydrochloride [ No CAS ]
  • [ 152533-47-6 ]
  • 64
  • (+/-)-exo-7-(Phenylmethyl)-7-azabicyclo<2.2.1>heptan-2-ol [ No CAS ]
  • [ 152533-47-6 ]
  • 65
  • (1S,2S,4R)-7-Aza-bicyclo[2.2.1]heptan-2-ol [ No CAS ]
  • [ 152533-47-6 ]
  • 66
  • (1R,2R,4S)-7-Benzyl-7-aza-bicyclo[2.2.1]heptan-2-ol [ No CAS ]
  • [ 152533-47-6 ]
  • 68
  • [ 152533-47-6 ]
  • (1R,2R,4S)-2-(6-Chloro-pyridin-3-yl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester [ No CAS ]
  • 71
  • (+/-)-trans-1,2-Epoxy-4-<N-(phenylmethyl)amino>cyclohexane [ No CAS ]
  • [ 152533-47-6 ]
  • 72
  • N-Benzyl-2,2,2-trifluoro-N-(7-oxa-bicyclo[4.1.0]hept-3-yl)-acetamide [ No CAS ]
  • [ 152533-47-6 ]
  • 73
  • [ 24424-99-5 ]
  • [ 910332-68-2 ]
  • [ 152533-47-6 ]
YieldReaction ConditionsOperation in experiment
64% With hydrogenchloride; triethylamine; In ethanol; dichloromethane; Example 12 Synthesis of 7-(t-butoxycarbonyl)-7-azabicyclo[2.2.1]heptan-2-one To 180 mg (0.970 mmol) of the diastereomer mixture obtained in Example 10, 7-(t-butoxycarbonyl)-3-methoxycarbonyl-7-azabicyclo[2.2.1]heptan-2-one, was added 3 ml of 10% HCl and the resulting mixture was heated under reflux at 100 C. for 3.5 hours. After completion of the reaction the solvent was evaporated in vacuo and the remaining water was removed by azeotropic distillation with ethanol. The crude product obtained was dissolved with 10 ml of dry methylene chloride, 169 ml (1.68 mmol) of Et3N and 292 mg (1.34 mmol) of (Boc)2O were added to the solution and the resulting mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was poured into a saturated aqueous sodium chloride solution, then extracted with chloroform, the extract was dried with Na2SO4, then filtrated and the solvent was evaporated in vacuo. The crude product thus obtained was purified by silica gel chromatography (AcOEt:hexane=1:3) to obtain 91.0 mg of 7-(t-butoxycarbonyl)-7-azabicyclo[2.2.1]heptan-2-one. Yield 64%. Colorless oil (solidifies on standing); mp: 60-62 C.; H1-NMR (CDCl3, 300 MHz) delta: 4.55 (t, J=4.5 Hz, 1H), 4.24 (d, J=4.9 Hz, 1H), 2.50-2.43 (m, 1H), 2.09-1.51 (m, 5H), 1.53 (s, 9H); IR (CHCl3): 1760, 1690 cm-1; FAB-MS m/z 212[M+H]+; HRMS 212.1287: C11H15O3N[M+H]+ 212.1297
  • 74
  • [ 1779-49-3 ]
  • [ 152533-47-6 ]
  • (+/-)-7-(1,1-dimethyl-ethoxycarbonyl)-7-azabicyclo[2.2.1]-heptan-2-ylidene [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With potassium tert-butylate; In benzene; Methyl triphenylphosphonium bromide (1.55 g, 4.34 mmol) was added to a stirred solution of potassium tert-butoxide (0.53 g, 4.34 mmol) in absolute benzene (8.0 mL). The mixture was refluxed for 15 minutes and most of the solvent was evaporated off. Ketone 83 (0.83 g, 3.93 mmol) was added to the remaining slurry at 90 C. The reaction mixture was stirred at 90 C. for 2 hours, cooled, and partitioned between H2 O (25 mL) and Et2 O (80 mL). The aqueous layer was extracted with Et2 O (3*80 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by chromatography (10% EtOAc/hexanes) to give compound 84 (0.52 g, 63%) as a clear oil. Rf 0.72 (10% EtOAc/hexanes). 1 H-NMR (CDCl3, 300 MHz) delta 4.93 (s, 1 H), 4.73 (s, 1 H), 4.50-4.36 (m, 1 H), 4.34-4.20 (m, 1 H), 2.53-1.54 (m, 5 H) 1.43 (s, 9 H).
63% With potassium tert-butylate; In benzene; Methyl triphenylphosphonium bromide (1.55 g, 4.34 mmol) was added to a stirred solution of potassium tert-butoxide (0.53 g, 4.34 mmol) in absolute benzene (8.0 mL). The mixture was refluxed for 15 minutes and most of the solvent was evaporated off. Ketone 83 (0.83 g, 3.93 mmol) was added to the remaining slurry at 90 C. The reaction mixture was stirred at 90 C. for 2 hours, cooled, and partitioned between H2 O (25 mL) and Et2 O (80 mL). The aqueous layer was extracted with Et2 O (3*80 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by chromatography (10% EtOAc/hexanes) to give compound 84 (0.52 g, 63%) as a clear oil. Rf 0.72 (10% EtOAc/hexanes). 1 H-NMR (CDCl3, 300 MHz) delta 4.93 (s, 1 H), 4.73 (s, 1 H), 4.50-4.36 (m, 1 H), 4.34-4.20 (m, 1 H), 2.53-1.54 (m, 5 H) 1.43 (s, 9 H).
  • 75
  • [ 152533-47-6 ]
  • [ 1610723-00-6 ]
  • 76
  • [ 152533-47-6 ]
  • [ 1610715-13-3 ]
  • [ 1610715-12-2 ]
  • 77
  • [ 152533-47-6 ]
  • [ 510748-36-4 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; In methanol; at 0 - 25℃;Inert atmosphere; To a solution of rac-<strong>[152533-47-6]tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate</strong> (500 mg, 2.37 rnrnol; a synthesis of this bicycle is described in WO 2005/000806) in MeOH (4.7 mL) at 0 C was added sodium borohydride (134 mg, 3.55 mmcl) in several portions. The reaction mixture was stirred at 0 C for 1 hr and warmed to room temperature and continuously stirred overnight. The mixture was quenched with saturated aq. amrnonium chloride aqueoussolution and the methanol was evaporated under reduced pressure. The resulting aqueous residue was extracted with CH2C12 (3x), and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated to give rac-tert-butyl 2-hydroxy-7- azabicyclo [2.2.1 ]heptane-7-earboxylate as a mixture of diastereomers which was used without further purification. To a solution of rac-tert-butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7- carboxylate (243 mg, 1.14 mrnol) in THF (9 mL) was added a 60% suspension of NaH in mineral oil (150 mg, 3.75 mmol). The reaction was stirred at 0 C for 30 mm, after which Intermediate IV (250 mg, 0.91 mrnol) was added. The reaction was allowed to warm to RT and was stirred for 15 h. The reaction was then quenched with water (10 niL) and extracted withethyl acetate (2 xl 0 niL). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (30 to 100% ethyl acetate/hexanes) to provide rac-tert-butyl 2-((9-ethyl-8-(2-methylpyrimidin-5-yl)-9H-purin-6-yl)oxy)-7-azabicyclo [2.2.1 ]heptane-7-carboxylate. MS (El) Calc?d for C23H30N703 [M-bH], 452; found, 452.
With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 17h; Step 7: To a solution of <strong>[152533-47-6]tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate</strong> (500 mg, 2.37 mmol) in methanol (4.7 mL) at 0 C. was added sodium borohydride (134 mg, 3.55 mmol). The reaction mixture was stirred at 0 C. for 1 hour and then stirred for 16 hours at room temperature. The mixture was quenched with saturated aqueous ammonium chloride and concentrated. The resulting residue was extracted with DCM (3*) and the combined extracts were dried over sodium sulfate, filtered, and concentrated to afford tert-butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate. 1H NMR (500 MHz, CDCl3) delta 4.35 (broad, 1H), 4.13 (s, 2H), 2.28-2.19 (m, 1H), 2.18-2.12 (m, 1H), 1.83-1.75 (m, 1H), 1.71-1.68 (m, 1H), 1.66-1.56 (m, 1H), 1.56-1.48 (m, 1H), 1.44 (s, 9H), 1.05 (dd, J=3.4, 12.7, 1H).
  • 78
  • [ 152533-47-6 ]
  • [ 1610715-09-7 ]
  • 79
  • [ 152533-47-6 ]
  • [ 1610715-11-1 ]
  • 80
  • [ 152533-47-6 ]
  • 7-azabicyclo[2.2.1]heptan-2-ol [ No CAS ]
  • 81
  • 7-aza-bicyclo[2.2.1]heptan-2-one [ No CAS ]
  • [ 24424-99-5 ]
  • [ 152533-47-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 2h; Step 6: Into a 2000-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 7-aza-bicyclo[2.2.1]heptan-2-one (39.72 g, 357.39 mmol, 1.00 equiv), DCM (400 mL), triethylamine (146.47 g, 1.45 mol, 4.05 equiv), and (Boc)2O (156.01 g, 714.82 mmol, 2.00 equiv). The resulting solution was stirred for 2 h at room temperature. The resulting mixture was washed with 1*400 mL of Na2CO3 solution and 1*400 mL of H2O. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatograpy (ethyl acetate/petroleum ether, 10:1) to afford tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate.
2.4 g With triethylamine; In dichloromethane; at 20℃; for 16h;Inert atmosphere; A mixture of 3-oxo-7-aza-bicyclo[2.2.1]heptane-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester (5.0 g, 18.5 mmol) and 10% solution HCl in water (150 mL) was heated at 100 C for 2 h. Progress of the reaction was monitored by LCMS analysis, upon completion of the starting material, solvent was removed in vacuo to provide a yellow residue. The residue obtained was taken up in dichloromethane (150 mL) triethylamine (11.2 g, 111 mmol) was added at 0 C under N2 atmosphere followed by Di-tert-butyldicarbonate (8.1 g, 37.1 mmol). Reaction mixture was allowed to stir at RT for 16 h. After the completion of the reaction as monitored by the LCMS analysis, reaction mass was diluted with dichloromethane (100 mL) and washed with water, brine solution and dried over anhydrous Na2SO4. The crude product obtained was purified by the flash column chromatography (230-400 size mesh) using 15-16% ethyl acetate in pet ether to afford the pure product as off white solid (2.4 g, 61%). 1H NMR (400 MHz, DMSO-d6): delta 4.41-4.38 (m, 1 H), 4.06-4.02 (m, 1 H), 2.39-2.34 (m, 1 H), 2.10 (s, 0.5H), 2.05 (s, 0.5H), 1.92-1.86 (m, 1 H), 1.83-1.76 (m, 1 H), 1.65-1.49 (m, 2H), 1.38 (s, 9H). LCMS: (Method A) 112.2 (M-Boc+H)+, Rt. 3.5 min, 97.8% (Max)
  • 82
  • [ 152533-47-6 ]
  • (2-endo)-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester [ No CAS ]
  • (2-endo)-2-hydroxy-7-azabicyclo[2.2.1]heptanes-7-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
33%; 41% With platinum(IV) oxide; hydrogen; triethylamine; In ethanol; at 20℃; for 24h; To a stirred solution of <strong>[152533-47-6]2-oxo-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester</strong> (2.4 g, 11.3 mmol) in ethanol (48 mL) was charged platinum oxide (0.140 g, Hindustan Platinum) followed by triethylamine (3.45 g, 34.1 mmol) at RT under N2 atmosphere. Nitrogen atmosphere was replaced by hydrogen and allowed to stir at RT for 12 h. Progress of the reaction was monitored by TLC and LCMS analysis. Analytic showed that reaction was not complete. Platinum oxide (0.070 g) was charged again and continued the stirring for 12 h. Upon completion of the reaction, catalyst was removed by filtration. The solvent was evaporated under vacuo to get the crude product. The crude product obtained was purified by the flash column chromatography (230-400 size mesh) using 28-29% ethyl acetate in n-hexane to afford the first eluting fraction as pale yellow liquid (0.8 g, 33%), and 30-32% ethyl acetate in n-hexanes to afford the second eluting fraction as off white solid (1.0 g, 41%). Based on NMR experiment, the first eluting compound was attributed to the endo isomer and the second eluting compound to the exo isomer. [0111] First eluting compound (endo): 1H NMR (400 MHz, DMSO-d6): delta 5.03 (d, J = 4.0 Hz, 1 H), 4.05 (dd, J = 9.2, 4.0 Hz, 1 H), 3.93 (t, J = 4.8 Hz, 1 H), 3.87 (t, J= 4.0 Hz, 1 H), 2.09-1.97 (m, 2H), 1.62-1.52 (m, 1 H), 1.49-1.39 (m, 2H), 1.37 (s, 9H), 0.93 (dd, J = 12.4, 3.2 Hz, 1 H). LCMS: (Method A) 114.3 (M-Boc+H)+, Rt. 3.1 min, 98.2% (ELSD). Second eluting compound (exo): 1H NMR (400 MHz, DMSO-d6): delta 4.77 (d, J = 3.6 Hz, 1 H), 4.01 (t, J = 4.4 Hz, 1 H), 3.84 (d, J = 4.8 Hz, 1 H), 3.71 (s, 1 H), 1.71-1.66 (m, 1 H), 1.61-1.47 (m, 2H), 1.37 (s, 9H), 1.36-1.32 (m, 1 H), 1.19 (d, J= 8.0 Hz, 2H). LCMS: (Method A) 114.3 (M-Boc+H)+, Rt. 2.9 min, 99 % (ELSD)
  • 83
  • [ 502506-71-0 ]
  • [ 152533-47-6 ]
  • 84
  • 3-oxo-7-aza-bicyclo[2.2.1]hept-5-ene-2,7-dicarboxylic acid 7-<i>tert</i>-butyl ester 2-ethyl ester [ No CAS ]
  • [ 152533-47-6 ]
  • 85
  • C14H21NO5 [ No CAS ]
  • [ 152533-47-6 ]
YieldReaction ConditionsOperation in experiment
71.8% A mixture of compound 84d (2.80 g, 9.88 mmol,1.00 eq,) in 10% HC1 (5 mE) was stirred at 10 C. for 6 hours, and concentrated under reduced pressure at 60 C. The residue was diluted with DCM (50 mE), and TEA (5 g, 49.4 mmol) and (Boc)20 (3.23 g, 14.82 mmol) were added. The reaction mixture was stirred overnight at room temperature, then quenched with water and extracted with DCM (50 mEx3). The combined organic phase was washed with saturated brine (50 mEx2), dried with anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (PE/EtOAc) to afford compound 84e (1.50 g, 7.lOmmol, 71.8% yield) as a yellow oil. ?H NMR (400 MHz, CDC13) 4.56 (brs, 1H), 4.25 (d, J=4.77, 1H), 2.47 (dd, J=17.44, 5.40, 1H), 1.90-2.09 (m, 3H), 1.53-1.71 (m, 2H), 1.45 (s, 9H).
  • 86
  • [ 152533-47-6 ]
  • N-(3-(6-(7-azabicyclo[2.2.1]hept-2-en-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-fluorophenyl)-2,4-dimethyloxazole-5-carboxamide [ No CAS ]
  • 87
  • [ 152533-47-6 ]
  • C28H26FN7O4 [ No CAS ]
  • 88
  • C8H6F6N2O6S2 [ No CAS ]
  • [ 152533-47-6 ]
  • C12H14F3NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% To a mixture of compound 84e (211 mg, 998.7tmol, 1.00 eq.) in THF (10 mE) was added EDA (160.48 mg, 1.50 mmol, 1.50 eq.) dropwise at -78 C. under N2. The resulting mixture was stirred at -78 C. for 3 hours, then N-(5-chioropyridin-2-yl)-O-((trifluoromethyl)sulfonyl)-N-(((trifluoromethyl)sulfonyl)oxy) (784.39 mg, 2.00 mmol, 2.00 eq.) was added in one portion and the mixture was stirred at -78 C. for 3 hours. The reaction mixture was slowly warmed up to room temperature and stirred for 2 days, quenched with a saturated NH4CI solution (20 mE) and extracted with EtOAc (20 mEx2). The combined organic layers were washed with brine (20 mE), dried and concentrated. The residue was purified by TEC (PE/EtOAc: 10/1) to afford compound 84f (100 mg, 279.8 tmol, 28% yield) as a yellow oil. ?H NMR (400 MHz, CDC13) 5.96 (brs, 1H), 4.76 (brs, 1H), 4.68 (d, J=2.51, 1H), 1.94-2.11 (m, 2H), 1.28-1.55 (m, 11H).
  • 89
  • [ 106-95-6 ]
  • [ 152533-47-6 ]
  • tert-butyl 2-allyl-3-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
NaHIVIDS (10 mL, 10 mmol, 1M in THF) was added to a mixture of tert-butyl 2-oxo-7- azabicyclo[2.2.1]heptane-7-carboxylate (2 g, 9.5 mmol) in THF (30 mL) at -40 C underN2 atmosphere. The mixture was stirred at -40 C for 0.5 hours. Then pyrrolidine (0.34 g, 4.7 mmol) inTHF (1 mL) was added dropwise to the mixture at -40 C. One minute later, 3-bromoprop-1-ene (0.86 mL, 9.9 mmol) in THF (1 mL) was dropwise added to the mixture at -40 C under N2 and stirred at -40 C for 0.5 h then stirred at 25 C for 14 h. The mixture was quenched with water. The mixture was extracted with EtOAc, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, then filtered and concentrated in vacuum to give crude product, which was used into next step directly without further purification. LCMS (CioHi4NO3 (ES, m/z): 196 [M+HC 4H8]t
  • 90
  • [ 152533-47-6 ]
  • rel-(3S,4R)-2-amino-3-(3-boronopropyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid heptafluorobutyrate [ No CAS ]
  • 91
  • [ 152533-47-6 ]
  • 3-allyl-7-azabicyclo[2.2.1]heptan-2-one [ No CAS ]
  • 92
  • [ 152533-47-6 ]
  • rel-(1R,2S)-benzyl 2-allyl-3-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate [ No CAS ]
  • 93
  • [ 152533-47-6 ]
  • rel-(35,4R)-benzyl 2-acetamido-3-allyl-2-(tert-butylcarbamoyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate [ No CAS ]
  • 94
  • [ 152533-47-6 ]
  • rel-benzyl (3S,4R)-2-acetamido-2-(tert-butylcarbamoyl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)-7-azabicyclo[2.2.1]heptane-7-carboxylate [ No CAS ]
  • 95
  • [ 152533-47-6 ]
  • [ 152614-12-5 ]
YieldReaction ConditionsOperation in experiment
61% With sodium tetrahydroborate; In methanol; at 20℃;Inert atmosphere; To a 100 mL round-bottom flask purged with N2 was placed a solution of tert-butyl 2- oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate (900 mg, 4.26 mmol) in MeOH (15 mL) then NaBH4 (243 mg, 6.4 mmol) was added. The resulting solution was stirred at rt overnight. The reaction was quenched by the addition of 100 mL of water, then the mixture was extracted with EtOAc (3x100 mL). The organic extracts were combined, washed with brine (3x100 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography using a silica gel column eluting with EtOAc/petroleum ether (1:4) affording 550 mg (61%) of the title compound as a colorless oil. Mass Spectrum (LCMS, ESI pos.): Calcd. for C11H20NO3: 214 (M+H); found: 214.
  • 96
  • [ 152533-47-6 ]
  • tert-bulyl (1R,2R,4S)-2-methoxy-7-azabicyclo[2.2.1]heptane-7-carboxylate [ No CAS ]
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 152533-47-6 ]

Amides

Chemical Structure| 741737-30-4

[ 741737-30-4 ]

tert-Butyl 2-methyl-3-oxopiperidine-1-carboxylate

Similarity: 0.95

Chemical Structure| 117625-90-8

[ 117625-90-8 ]

1-Boc-2-Formylpyrrolidine

Similarity: 0.93

Chemical Structure| 185099-67-6

[ 185099-67-6 ]

tert-Butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate

Similarity: 0.91

Chemical Structure| 73193-55-2

[ 73193-55-2 ]

Ethyl 2-methyl-3-oxopyrrolidine-1-carboxylate

Similarity: 0.91

Chemical Structure| 101385-93-7

[ 101385-93-7 ]

N-Boc-3-Pyrrolidinone

Similarity: 0.91

Ketones

Chemical Structure| 741737-30-4

[ 741737-30-4 ]

tert-Butyl 2-methyl-3-oxopiperidine-1-carboxylate

Similarity: 0.95

Chemical Structure| 185099-67-6

[ 185099-67-6 ]

tert-Butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate

Similarity: 0.91

Chemical Structure| 73193-55-2

[ 73193-55-2 ]

Ethyl 2-methyl-3-oxopyrrolidine-1-carboxylate

Similarity: 0.91

Chemical Structure| 101385-93-7

[ 101385-93-7 ]

N-Boc-3-Pyrrolidinone

Similarity: 0.91

Chemical Structure| 98977-36-7

[ 98977-36-7 ]

1-Boc-3-Piperidinone

Similarity: 0.89

Related Parent Nucleus of
[ 152533-47-6 ]

Aliphatic Heterocycles

Chemical Structure| 117625-90-8

[ 117625-90-8 ]

1-Boc-2-Formylpyrrolidine

Similarity: 0.93

Chemical Structure| 185099-67-6

[ 185099-67-6 ]

tert-Butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate

Similarity: 0.91

Chemical Structure| 73193-55-2

[ 73193-55-2 ]

Ethyl 2-methyl-3-oxopyrrolidine-1-carboxylate

Similarity: 0.91

Chemical Structure| 157634-02-1

[ 157634-02-1 ]

tert-Butyl 2-formylpiperidine-1-carboxylate

Similarity: 0.89

Chemical Structure| 98977-36-7

[ 98977-36-7 ]

1-Boc-3-Piperidinone

Similarity: 0.89

Other Aliphatic Heterocycles

Chemical Structure| 185099-67-6

[ 185099-67-6 ]

tert-Butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate

Similarity: 0.91

Chemical Structure| 512822-27-4

[ 512822-27-4 ]

tert-Butyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate

Similarity: 0.89

Chemical Structure| 188975-88-4

[ 188975-88-4 ]

tert-Butyl 4-oxoazepane-1-carboxylate

Similarity: 0.88

Chemical Structure| 198835-06-2

[ 198835-06-2 ]

tert-Butyl 5-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Similarity: 0.85

Chemical Structure| 879687-92-0

[ 879687-92-0 ]

tert-Butyl 4-oxohexahydro-1H-isoindole-2(3H)-carboxylate

Similarity: 0.85