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[ CAS No. 841302-36-1 ] {[proInfo.proName]}

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Chemical Structure| 841302-36-1
Chemical Structure| 841302-36-1
Structure of 841302-36-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 841302-36-1 ]

CAS No. :841302-36-1 MDL No. :MFCD29921822
Formula : C13H15NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 217.26 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 841302-36-1 ]

* 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 [ 841302-36-1 ]

[ 841302-36-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 593-71-5 ]
  • [ 25070-74-0 ]
  • [ 841302-36-1 ]
YieldReaction ConditionsOperation in experiment
78% With diethylzinc In diethyl ether at -40 - 20℃; 3.3 To a solution of Step 2 olefin (4.99 g, 24.5 MMOL) in Et20 (164 mL) at 0 °C was slowly added diethylzinc (116 mL of a 1.0 M solution in hexane, 116 MMOL, 4.75 equiv), followed by ICH2CI (17.1 mL, 235 mmol, 9.58 equiv). The resulting reaction mixture was stirred at 0 °C for 6 h, kept at-40 °C overnight and then stirred at rt for 4 h. The reaction was then quenched by the addition of 25% NH4CI (65 mL) and extracted with Et20 (3 x 300 mL). The combined organic extracts were washed with 25% NH4CI (65 mL), brine (65 mL), dried (NA2SO4), filtered and concentrated under reduced pressure to give the crude product (15 g) as a yellow oil. Purification of the crude product by flash chromatography (silica gel, CH2CI2) generated the cyclopropyl product (4.17 g, 78%) as a colorless liquid : LC/MS M/Z 218 [M+H] + ; H NMR (CDCI3, 400 MHz) 6 7.26-7. 37 (m, 5H), 5.30 (s, 2H), 3.73 (t, 1H, J= 8. 8 Hz), 3.45-3. 55 (m, 1H), 3.03-3. 10 (m, 1H), 2.05-2. 15 (m, 1H), 191.-1. 97 (ddd, 1H, J = 12. 8,8. 4,2. 6 Hz), 1. 51-1. 59 (dt, 1H, J = 14.1, 5.7 Hz), 0.68-0. 76 (m, 1H), 0.53-0. 58 (m, 1H).
  • 2
  • [ 841302-36-1 ]
  • [ 841302-37-2 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogenchloride; hydrogen In ethanol; ethyl acetate at 20℃; for 24h; 4.7 {5-[3-(2-Aza-bicyclo[3.1.0]hex-2-yl)-propoxy]-1H-indol-2-yl}-morpholin-4-yl-methanone Step 7: 2-Aza-bicyclo[3.1.0]hexane hydrochloride. A mixture of 2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid benzyl ester (example 4, step 6, 130 mg, 1.0 eq.) and palladium on activated charcoal (10% in mass, 64 mg, 0.1 eq.), in a solution of hydrochloric acid in ethyl acetate (2.23M, 1 mL) and ethanol (10 mL) was vigorously stirred 24 h at room temperature under an atmosphere of hydrogen (1 Atm). The reaction mixture was filtered on a dicalite pad and the pad was washed with ethanol. The filtrate was evaporated in vacuo and purified by precipitation with dichloromethane/tert-butyl-methylether to yield 69 mg (96%) of the desired product as brown solid. MS (m/e): 82 (M-H-, 100%).
79% With hydrogenchloride; hydrogen In ethanol; water at 20℃; for 25h; 3.4 A mixture of the Step 3 compound (160 mg, 0.74 MMOL), 1 N HCI (0.8 mL, 0.8 mmol, 1.08 equiv) and 10% Pd/C (32 MMOL, 43 equiv) in 95% EtOH (13 mL) was stirred at rt under hydrogen atmosphere for 19 h. Another 20 mg of 10% Pd/C was added and the mixture was stirred under hydrogen atmosphere for additional 6 h. The reaction mixture was diluted with EtOH (10 mL) and filtered on a celite pad. The filtrates were concentrated under reduced pressure to give the HCI salt of expected product (95 mg, 79%) as a white solid : H NMR (D20, 400 MHZ) 6 3. 30 (dt, 1H, J= 12.8, 5.1 Hz), 3.15 (ddd, 1 H, J = 6. 0,5. 8, 2.9 Hz), 2.76 (q, 1 H, J = 9.9 Hz), 1.97-2. 06 (m, 2H), 1.67-1. 75 (m, 1 H), 0.68- 0.76 (m, 2H).
  • 3
  • [ 593-71-5 ]
  • [ 68471-57-8 ]
  • [ 841302-36-1 ]
YieldReaction ConditionsOperation in experiment
50% Step 6: 2-Aza-bicyclo[3.1.0]hexane-2-carboxylic acid benzyl ester To a cold (0 C.) solution of <strong>[68471-57-8]2,3-dihydro-pyrrole-1-carboxylic acid benzyl ester</strong> (example 4, step 5, 300 mg, 1.0 eq.) in diethyl ether was slowly added a solution of diethylzinc in hexanes (1M, 7 mL, 4.75 eq.), followed by chloroiodomethane (1.1 mL, 10 eq.). The reaction mixture was stirred 3 h at 0 C., allowed to warm up to room temperature and stirred an additional 3 h. The reaction mixture was partitioned between an aqueous solution of ammonium chloride and diethyl ether. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with brine, dried over sodium sulphate and evaporated in vacuo and purified on silica, eluding with a 1:1 to 1:3 gradient of cyclohexane/dichloromethane, to yield 160 mg (50%) of the desired product as colourless oil. MS (m/e): 218.5 (MH+, 100%)
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