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Chemical Structure| 75390-09-9
Chemical Structure| 75390-09-9
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CAS No. :75390-09-9 MDL No. :MFCD09608024
Formula : C11H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :SOOHWZBGWRAMJJ-UHFFFAOYSA-N
M.W : 175.23 Pubchem ID :9815370
Synonyms :

Safety of [ 75390-09-9 ]

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

Application In Synthesis of [ 75390-09-9 ]

* 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 [ 75390-09-9 ]
  • Downstream synthetic route of [ 75390-09-9 ]

[ 75390-09-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 6913-92-4 ]
  • [ 75390-09-9 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With sulfuric acid In methanol; water at 0℃; for 0.0833333 h;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In methanol; water at 20℃; for 18 h;
Stage #3: With sodium hydroxide In water
Was synthesised according to published methods:.
To a solution of 1-benzyl-3-pyrroline (5.0 g, 31.40 mmol) in methanol (20 ml) cooled at 0°C, water was added (5 ml) and H2S04 96percent (2 ml).
The solution was stirred 5 min. and 3-chloroperoxybenzoic acid (10.0 g, 40.56 mmol) was added in portions.
The suspension was stirred at r.t. for 18 h.
Methanol was evaporated and the aquose solution was neutralized with aq. NaOH 10 percent until pH=7.
The suspension was extracted with dichloromethane and the organic phase was washed with water and saturated solution of NaCl, dried over Na2SO4, filtered and concentrated to afford pure product (4.35 g, 80percent) as yellow oil.
1H NMR (400 MHz, CDCl3): δ (ppm) 7.49-7.23 (m, 5H), 3.81 (s, 2H), 3.66 (s, 2H), 3.23 (d, J=12Hz, 2H), 2.72 (d, J=12Hz, 2H).
77% With sulfuric acid; 3-chloro-benzenecarboperoxoic acid In water; acetone at 0 - 20℃; for 50 h; To an ice-cooled solution of 1-benzyl pyrroline (0. 01 mol), 98percent H2SO4 (0.012 mol), water (1.5 g), and acetone (10 mL) in a round bottom flask was added 77percent m- CPBA (0. 013 mol) with stirring, and allowed to react for about 50 h at room temperature. After completion of the reaction (TLC monitor), acetone was evaporated under reduced pressure, and the mixture was neutralized by 1M NAOH, and extracted with toluene (30 mL X3). The precipitates that appeared were filtered, and the filtrate was repeatedly washed with water (30 mL x2). After the solvent was evaporated under reduced pressure, pure product was obtained in 77percent yield via column chromatography (silica gel, CH2CL2 : EtOAc: MeOH, 7.5 : 2.00 : 0.5).
77% With sulfuric acid; 3-chloro-benzenecarboperoxoic acid In water; acetone at 20℃; for 50 h; Example 2Synthesis of 3-benzyl-6-oxa-3-aza-bicyclo[3.1.0]hexane (1-2) To an ice-cooled solution of 1 -benzyl pyrroline (0.01 mol), 98percent H2SO4 (0.012 mol), water (1.5 g), and acetone (10 mL) in a round bottom flask was added 77percent m-CPBA (0.013 mol) with stirring, and allowed to react for about 50 h at room temperature. After completion of the reaction (TLC monitor), acetone was evaporated under reduced pressure, and the mixture was neutralized by 1M NaOH, and extracted with toluene (30 mL .x.3). The precipitates that appeared were filtered, and the filtrate was repeatedly washed with water (30 mL .x.2). After the solvent was evaporated under reduced pressure, pure product was obtained in 77percent yield via column chromatography (silica gel, CH2Cl2:EtOAc :MeOH, 7.5: 2.00: 0.5).
38%
Stage #1: With sulfuric acid; 3-chloro-benzenecarboperoxoic acid In water; acetone at 0 - 20℃; for 48 h;
Step 1 : To an ice-cooled solution of 26a (4.77g, 30mmol), 98percent H2SO4 (1.95mL), H2O (4.5mL) and acetone (3OmL) was added 85percent mCPBA (7.9 Ig, 39mmol) with stirring. The mixture was allowed to react for 48hrs at r.t. Acetone was evaporated and the mixture was neutralized with IN aq. NaOH and extracted with toluene. The organic phase was dried over anhy. MgSO4 and evaporated. The residue was purified by column chromatography (EArPE=I :4) to provide 26b (2.Og, 38percent).
38%
Stage #1: With sulfuric acid; 3-chloro-benzenecarboperoxoic acid In water; acetone at 20℃; for 48 h;
Stage #2: With sodium hydroxide In water
Example 26 Preparation of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1-benzyl-4-hydroxy-pyrrolidin-3-yl)-amide Preparation of 4-Amino-1-benzyl-pyrrolidin-3-ol Step 1: To an ice-cooled solution of 26a (4.77 g, 30 mmol), 98percent H2SO4 (1.95 mL), H2O (4.5 mL) and acetone (30 mL) was added 85percent mCPBA (7.91 g, 39 mmol) with stirring. The mixture was allowed to react for 48 hrs at r.t. Acetone was evaporated and the mixture was neutralized with 1N aq. NaOH and extracted with toluene. The organic phase was dried over anhy. MgSO4 and evaporated. The residue was purified by column chromatography (EA:PE=1:4) to provide 26b (2.0 g, 38percent).

Reference: [1] Patent: EP1849781, 2007, A1, . Location in patent: Page/Page column 90
[2] Patent: WO2005/26111, 2005, A2, . Location in patent: Page/Page column 7
[3] Patent: WO2008/42353, 2008, A1, . Location in patent: Page/Page column 11; 12
[4] Journal of the American Chemical Society, 2008, vol. 130, # 12, p. 3900 - 3914
[5] Patent: WO2008/33562, 2008, A2, . Location in patent: Page/Page column 55
[6] Patent: US2009/76005, 2009, A1, . Location in patent: Page/Page column 24
[7] Journal of the Chemical Society, Chemical Communications, 1995, # 3, p. 293 - 294
  • 2
  • [ 100-46-9 ]
  • [ 75390-09-9 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 47 h; To 1,4-dimethanesulfonyloxy-3,4-epoxybutane (3e)(3e) (29.51 g, 113 mmol) were added 58.5 ml of tetrahydrofuran..
A solution prepared by adding 20 ml of tetrahydrofuran to benzylamine (37.0 ml, 3.0eq.) was added dropwise to the resulting mixture on a water bath with stirring..
The container therefor was washed clean with 10 ml of tetrahydrofuran..
After stirring forty seven hours at room temperature, the reaction solution was poured into 153 ml of 2N sodium hydroxide..
The resulting product was extracted twice with 118 ml of t-butyl ether..
The upper layer of the solution was dried over anhydrous magnesium sulfate, and dried at 40 °C in vacuo, to obtain 43.8 g of a yellow solution..
The resulting crude product was purified with silica gel column chromatography (silica gel: (Wako gel C-200) 526 g, developing solution: t-butylmethyl ether), to obtain 17.
9 g of the titled compound in the form of yellow liquid (90 percent yield).1H-NMR(400MHz, CD3CN) d: 2.48 (2H, d, J=11.6 Hz), 3.03 (2H, d, J=11.6 Hz), 3.55 (2H, s), 3.64 (2H, s,) 7.21-7.32 (5H, m)
Reference: [1] Patent: EP1375465, 2004, A1, . Location in patent: Page 16
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