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Chemical Structure| 133111-56-5 Chemical Structure| 133111-56-5

Structure of 133111-56-5

Chemical Structure| 133111-56-5

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Product Details of [ 133111-56-5 ]

CAS No. :133111-56-5
Formula : C21H20ClN
M.W : 321.84
SMILES Code : CC1(C)CN2C=C(C(=C2C1)C1=CC=CC=C1)C1=CC=C(Cl)C=C1
MDL No. :MFCD17015338

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Application In Synthesis of [ 133111-56-5 ]

* 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 [ 133111-56-5 ]

[ 133111-56-5 ] Synthesis Path-Downstream   1~4

  • 2
  • [ 79-37-8 ]
  • [ 133111-56-5 ]
  • [ 156897-06-2 ]
YieldReaction ConditionsOperation in experiment
6. 6-(4-chlorophenyl)-2.2-dimethyl-7-phenyl-2.3-dihydro-l-H-pyrrolizin-5-yl-acetic acid (ML-3000).2^ 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-l-H-pyrrolizine (50 g,0.156 M) is dissolved with stirring in dry tetrahydrofuran. The assembly is blanketed with nitrogen atmosphere. The yellow colored solution is cooled to 10-15 0C and oxalyl chloride (31.6g, 0.24 M) is slowly added over a period of 10-15 min, such that the internal temperature is below 15 0C. After complete addition the green colored solution is <n="12"/>stirred at 18-25 0C for 20-30 min. The reaction mixture is then quenched carefully in Ice (80 g) such that the internal temperature does not exceed above 20 0C. The reaction mixture is then stirred at 20-30 0C for 5-10 min. The solution is diluted with diethylene glycol (27Og) and hydrazine (65g, 1.28 mol). The internal temperature is then raised gradually and solvent THF is distilled off during the process until the temperature reaches75-80 0C. The suspension is then cooled to 50-55 0C and KOH (113 g, 2.02 M) is added portion wise over a period of 30 min. The now yellowish liquid is then heated to 95-110 0C gradually. During the process excessive frothing is observed. Nitrogen is blown through the reaction mixture by means of a dip tube at an increased stirring speed. The temperature is then raised slowly to 140-145 0C and during the process aqueous distillate is collected. The batch is held at 130-145 0C for 2-3 hr. The reaction temperature is then cooled to 35-40 0C and water and diethyl ether are added. The mixture is stirred vigorously for 15-20 min and with the stirring switched off the layers are allowed to settle. The aqueous phase is separated cooled below 5 0C and acidified to pH 1 using a solution of HCl maintaining temperature below 10 0C. The separated solid is taken up in diethyl ether and "the ethereal extract is washed thoroughly with water. The ethereal extract is charcoalised before being evaporated under vacuo below 20 0C. The solid is slurried in heptane and is filtered under suction and washed with heptane. The product is dried in vacuum at 45^-55 0C.
  • 3
  • [ 49827-15-8 ]
  • [ 133111-56-5 ]
  • [ 262426-70-0 ]
YieldReaction ConditionsOperation in experiment
60 - 78% With dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide; In water; at 10 - 20℃; for 0.25 - 1.83333h;Cooling with cold water bath;Product distribution / selectivity; Example 13 7er-Butyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-lH-pyrrolizine-5- yl)acetate (IVc)Carrying out the procedure described in example 1 using ter<strong>[49827-15-8]t-butyl iodoacetate</strong> the desired product (IVc) was obtained in the yield of 78percent, melting temp. 165-167 °C. 1H-NMR spectrum (CDCl3): 1.29s, 6H (2xCH3); 1.46s, 9H (t-Bu); 2.84s, 2H (CH2); 3.41s, 2H (CH2); 3.75s, 2H (CH2); 7.03-7.26m, 9HAr. Example 14 Tert-Butyl 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-lH-pyrtauolizine-5- yl)acetate (IVc)Carrying out the procedure described in example 9 using tert-butyl bromoacetate the desired product (IVc) was obtained in the yield of 60percent, melting temp. 166-168 0C.
  • 4
  • [ 1003-85-6 ]
  • [ 133111-56-5 ]
 

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