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Chemical Structure| 1416134-48-9
Chemical Structure| 1416134-48-9
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Product Details of [ 1416134-48-9 ]

CAS No. :1416134-48-9 MDL No. :MFCD29918783
Formula : C17H24N2O7 Boiling Point : -
Linear Structure Formula :- InChI Key :PYUXATUBICTSNB-DFQHDRSWSA-N
M.W : 368.38 Pubchem ID :86675004
Synonyms :

Safety of [ 1416134-48-9 ]

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

Application In Synthesis of [ 1416134-48-9 ]

* 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 [ 1416134-48-9 ]
  • Downstream synthetic route of [ 1416134-48-9 ]

[ 1416134-48-9 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
65.4%
Stage #1: With sulfuric acid In ethyl acetate at -20 - -15℃; for 1 h;
Stage #2: With sodium tris(acetoxy)borohydride In ethyl acetate at -20 - -15℃; for 5 h;
Stage #3: at 45℃; for 2 h;
To stir,Thermometer in a 2000 ml four-necked flask500 grams of ethyl acetate,110.0 g (0.4 mole) of ethyl 5-benzyloxyiminopiperidine-2S-carboxylate (III2) are added,Maintaining negative 20°C to negative 15°C,201.0 grams of concentrated sulfuric acid (2.0 moles) was added dropwise.After dripping, stir for 1 hour.At negative 20°C,Add 190.0 g (0.9 moles) of sodium triacetoxyborohydride,The reaction was stirred at -20°C to -15°C for 5 hours.Keep the temperature below 0°C,Add 200 grams of water to quench the reaction;Ammonia is neutralized until the system has a pH of 7-8. Layered, withThe organic layer was washed twice with 100 g each time with saturated saline.The organic phase is concentrated to recover the solvent,Then 320 g of ethyl acetate was added to the resulting residue.160 grams of methanol,52.0 g (0.42 mol) of oxalic acid dihydrate,Heat to 45°C,After stirring for 2 hours, cool and filter.The filter cake was washed with 100 g of a mixture of ethyl acetate/methanol (2:1) and washed with 50 g of ethyl acetate. All the filtrates were combined and used in Example 5.The filter cake was vacuum dried to give 96.3 g of a single isomer5R-Benzyloxyaminopiperidine-2S-ethyl formate oxalate, chiral HPLC purity 99.6percent, yield 65.4percent.
Reference: [1] Patent: CN107540600, 2018, A, . Location in patent: Paragraph 0052-0054
[2] Patent: US2012/323010, 2012, A1, . Location in patent: Page/Page column 17-18
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YieldReaction ConditionsOperation in experiment
94%
Stage #1: at 0℃; for 1 h;
Stage #2: at 35℃;
Example 1fEthyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate (1:1) was prepared as described below.A slurry of benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate (1:1) (100 g, 232 mmol) in ethanol (2000 ml) was cooled to 0° C. A solution of sodium ethoxide in ethanol (216 ml, 580 mmol, 21 wt percent solution) was added slowly and the mixture was stirred for 1 h at 0° C. Acetic acid (13.3 ml, 232 mmol) was added and the mixture was concentrated under vacuum below 35° C. to a final volume of 300 ml. Ethyl acetate (700 ml) was added and the mixture was concentrated to 300 ml. This procedure was repeated twice. Water (1800 ml) was added to the mixture followed by aqueous ammonia (variable) until the pH of the aqueous layer was 7.5 to 8. The layers were separated and the aqueous layer was extracted with ethyl acetate (2.x.300 ml). The combined organic layers were washed with water (500 ml) and concentrated to a final volume of 300 ml. The solution was filtered and diluted with ethyl acetate (700 ml) and warmed to 35° C. A solution of oxalic acid dihydrate (30 g, 237 mmol) in acetone (200 ml) was added and the mixture was cooled to room temperature. The solids were isolated by filtration, washed with ethyl acetate and dried under vacuum at 35° C. to obtain ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate (1:1) as a white solid (80.7 g, 94percent).
Reference: [1] Patent: US2012/323010, 2012, A1, . Location in patent: Page/Page column 17
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Reference: [1] Patent: US2012/323010, 2012, A1,
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Reference: [1] Patent: US2012/323010, 2012, A1,
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Reference: [1] Patent: US2012/323010, 2012, A1,
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Reference: [1] Patent: US2012/323010, 2012, A1,
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Reference: [1] Patent: US2012/323010, 2012, A1,
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Reference: [1] Patent: US2012/323010, 2012, A1,
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