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Chemical Structure| 74892-82-3 Chemical Structure| 74892-82-3

Structure of 74892-82-3

Chemical Structure| 74892-82-3

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Product Details of [ 74892-82-3 ]

CAS No. :74892-82-3
Formula : C9H17NO2
M.W : 171.24
SMILES Code : O=C([C@@H]1NCC[C@@H](C)C1)OCC
MDL No. :MFCD03093749
InChI Key :GHBNOCBWSUHAAA-HTQZYQBOSA-N
Pubchem ID :10313307

Safety of [ 74892-82-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H227-H315-H319-H335
Precautionary Statements:P305+P351+P338

Application In Synthesis of [ 74892-82-3 ]

* 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 [ 74892-82-3 ]

[ 74892-82-3 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 1676-90-0 ]
  • [ 74892-82-3 ]
  • (2R,4R)-1-((S)-3-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-propionyl)-4-methyl-piperidine-2-carboxylic acid ethyl ester [ No CAS ]
  • 3
  • [ 2480-93-5 ]
  • [ 74892-82-3 ]
  • [ 174699-01-5 ]
  • 4
  • [ 74892-82-3 ]
  • [ 183679-12-1 ]
  • [ 183679-13-2 ]
  • 5
  • [ 74892-82-3 ]
  • [ 183679-09-6 ]
  • (2R,4R)-1-[(S)-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-2-(3-methyl-1,2,3,4-tetrahydro-quinoline-8-sulfonylamino)-butyryl]-4-methyl-piperidine-2-carboxylic acid ethyl ester [ No CAS ]
  • 6
  • [ 74892-82-3 ]
  • [ 174699-02-6 ]
  • 7
  • [ 74892-82-3 ]
  • (2R,4R)-1-[(S)-5-Amino-2-(3-methyl-1,2,3,4-tetrahydro-quinoline-8-sulfonylamino)-pentanoyl]-4-methyl-piperidine-2-carboxylic acid ethyl ester [ No CAS ]
  • 8
  • [ 74892-82-3 ]
  • (2R,4R)-1-[(S)-5-Cyanoamino-2-(3-methyl-1,2,3,4-tetrahydro-quinoline-8-sulfonylamino)-pentanoyl]-4-methyl-piperidine-2-carboxylic acid ethyl ester [ No CAS ]
  • 9
  • [ 74892-82-3 ]
  • C25H40N6O6S [ No CAS ]
  • 10
  • [ 74892-82-3 ]
  • [ 174699-04-8 ]
  • 11
  • [ 74892-82-3 ]
  • (2R,4R)-1-((S)-2-Amino-3-tert-butoxycarbonyl-propionyl)-4-methyl-piperidine-2-carboxylic acid ethyl ester [ No CAS ]
  • 12
  • [ 74892-82-3 ]
  • [ 1027984-73-1 ]
  • 13
  • [ 74892-82-3 ]
  • [ 1027037-83-7 ]
  • 14
  • [ 74892-82-3 ]
  • (2R,4R)-1-[(S)-3-[((S)-1-Carbamimidoyl-piperidin-3-ylmethyl)-carbamoyl]-2-(naphthalene-2-sulfonylamino)-propionyl]-4-methyl-piperidine-2-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
After 10 minutes, the hydrochloride salt of the title compound of Preparation 14 (1.7 g, 8.2 mmol) was added as a solution in dichloromethane (5 ml), dropwise, followed by the dropwise addition of a solution of N-methylmorpholine (0.9 g, 9 mmol) in dichloromethane (3 ml).
  • 19
  • [ 198641-56-4 ]
  • [ 74892-82-3 ]
YieldReaction ConditionsOperation in experiment
45% With 10% palladium hydroxide on charcoal; hydrogen; In ethanol; at 20℃; under 760.051 Torr; for 4h; To a solution of (1'S,2R,4R)-6 (2.5 g, 9 mmol) in ethanol (120 mL) 10% Pd(OH)2/C (0.27 g) was added. The hydrogenation was performed at room temperature and at atmospheric pressure. The reaction progress was monitored by TLC (chloroform/ methanol 9:1). After 4 h, the catalyst was removed by filtration through a Celite pad. Solvent evaporation at reduced pressure afforded the crude mixture that was purified by silica gel (1:20) column chromatography; pure title compound 2 (0.7 g, 45%) was recovered by elution with dichloromethane/methanol 98:2. 1H NMR (CDCl3) delta 0.96 (d, 3H, J = 6.50 Hz, CH3-4); 1.15 (m, 1H, H-5a), 1.32 (t, 3H, J = 7.2 Hz, CH3CH2); 1.42-1.54 (m, 1H, H-3); 1.5-1.69 (m, 2H, H-4, H-5b); 2.00-2.11 (m, 2H, H-3b and NH); 2.87 (m, 2H, H-6); 3.65 (m, 1H, H-2); 4.21 (q, 2H, J = 7.2 Hz, CH2CH3). [alpha]20D = -22 (c 5, ethanol) (lit.4 +24 for the enantiomer).
345 g With palladium 10% on activated carbon; hydrogen; iron(II) oxalate; acetic acid; In ethanol; at 30℃; under 3750.38 Torr; for 4h;Autoclave; The crude product (618 g) obtained in the previous step and ethanol (2 mL) were charged into a 5 L autoclave,Additional acetic acid (45 g), palladium on carbon catalyst (10% palladium loading, 15 g), 3 g iron oxalate,Access to H2, at 30 , 0.5MPa reaction 4h,filter,Catalyst recovery.The filtrate was concentrated under reduced pressure and added with ethyl acetate (1 L)Washed sequentially with saturated sodium carbonate solution (250 mL × 2), saturated brine (250 mL × 2)Dried over anhydrous sodium sulfate, filtered,The filtrate was concentrated under reduced pressure,Have a pale yellow liquid product.The resulting crude product was purified by distillation,Collected 89 ~ 90 / 10mmHg fractions,345 g of ethyl (2R, 4R) -4-methyl-2-piperidinecarboxylate was obtained in a yield of 91%.Optical rotation: (c = 5, EtOH)The total process yield above: 82.45%.Liquid chromatography determination:The (2R, 4R) -4-methyl-2-piperidinecarboxylic acid ethyl ester content was 99.3%.
  • 20
  • [ 74892-82-3 ]
  • [ 74874-07-0 ]
YieldReaction ConditionsOperation in experiment
33.7 g of CDMT and 334 ml of ethyl acetate are introduced in a reactor. The obtained solution is cooled at -10C and at this temperature 20.3 g of NMM are slowly added obtaining a suspension. After 40 minutes 55.6 g of N-Boc-N' -nitro-L-arginine and 117 ml of ethyl acetate are added. After about 1.5 hours 32.7 g of a mixture of ethyl (2R, 4R) -4-methylpiperidine-2-carboxylate and ethyl ( 2S, 4S ) -4-methylpiperidine-2-carboxylate(9/10) with a ratio of 97.7/2.3 (from example 4D) are added. After about 2.5 hours the reaction mixture is brought to 10C and kept under stirring at such temperature throughout the night. The suspension is filtered and the panel is washed with 222 ml of ethyl acetate. The organic solution is washed using 334 ml of a 5% sodium bicarbonate aqueous solution, 334 ml of hydrochloric acid 2N and 334 ml of saturated sodium chloride water.The organic phase is concentrated by distillation at reduced pressure obtaining 85 g of a mixture of the two ethyl ( 2R, 4R) -1- [ ( 2S ) -2- [ [ ( 1 , 1- dimethyletoxy) carbonyl] amino] -5-[ [ imino (nitroamino ) methyl ] amino ] -1-oxopentyl ] -4- methylpiperidine-2-carboxylate (5) and ethyl (2S,4S)-1- [ ( 2S ) -2- [ [ ( 1 , 1-dimethyletoxy) carbonyl ] amino ] -5- [ [ imino (nitroamino ) methyl ] amino ] -1-oxopentyl ] -4- methylpiperidine-2-carboxylate diastereoisomers (6) as olio (ratio 97, 7/2,3) .HPLC purity area as the sum of the two diastereoisomers: 98.2%. The product was used partly as it is in the subsequent step.
  • 21
  • ethyl 4-methyl-2-piperidinecarboxylate L-tartrate [ No CAS ]
  • [ 74892-82-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In water; ethyl acetate; at 20℃; for 1h; 65 g of a mixture of ethyl (2R, 4R) -4-methyl-2- piperidinecarboxylate L-tartrate (13) and ethyl (2S,4S)- 4-methyl-2-piperidinecarboxylate L-tartrate (14) (ratio 86/14), obtained in step 4A, 325 ml of ethyl acetate and 65 ml of water are introduced in a reactor. Cooling is carried out at 15C and an aqueous solution (130 ml) of potassium carbonate (31 g) is added in 5 minutes. The obtained biphasic solution is left under stirring at 20C for 1 hour, then the phases are separated, the aqueous phase is extracted once again using 130 ml of ethyl acetate, the two organic phases are concentrated by distillation at reduced pressure obtaining 29.4 g of ester (at 100%), with a 99.9% chemical purity. Molar yield 85%. Ethyl (2R, 4R) -4-methyl-2- piperidinecarboxylate (9) / ethyl ( 2S, 4S ) -4-methyl-2- piperidinecarboxylate (10) (87/13) ratio.
  • 22
  • [ 626-58-4 ]
  • [ 74892-82-3 ]
  • 23
  • [ 85796-64-1 ]
  • [ 74892-82-3 ]
  • 24
  • 4-methyl-2,3,4,5-tetrahydropyridine hydrochloride [ No CAS ]
  • [ 74892-82-3 ]
  • 25
  • 4-methyl-2-piperidinecarbonitrile [ No CAS ]
  • [ 74892-82-3 ]
  • 26
  • [ 2188-18-3 ]
  • [ 74892-82-3 ]
  • [ 74874-07-0 ]
YieldReaction ConditionsOperation in experiment
85 g 33.7 g of CDMT and 334 ml of ethyl acetate are introduced in a reactor. The obtained solution is cooled at -10 C. and at this temperature 20.3 g of NMM are slowly added obtaining a suspension. After 40 minutes 55.6 g of N-Boc-N?-nitro-L-arginine and 117 ml of ethyl acetate are added. After about 1.5 hours 32.7 g of a mixture of ethyl(2R,4R)-4-methylpiperidine-2-carboxylate and ethyl (2S,4S)-4-methylpiperidine-2-carboxylate (9/10) with a ratio of 97.7/2.3 (from example 4D) are added. After about 2.5 hours the reaction mixture is brought to 10 C. and kept under stirring at such temperature throughout the night. The suspension is filtered and the panel is washed with 222 ml of ethyl acetate. The organic solution is washed using 334 ml of a 5% sodium bicarbonate aqueous solution, 334 ml of hydrochloric acid 2N and 334 ml of saturated sodium chloride water. [0074] The organic phase is concentrated by distillation at reduced pressure obtaining 85 g of a mixture of the two ethyl (2R,4R)-1-[(2S)-2-[[(1,1-dimethyletoxy)carbonyl]amino]-5-[[imino(nitroamino)methyl]amino]-1-oxopentyl]-4-methylpiperidine-2-carboxylate (5) and ethyl (2S,4S)-1-[(2S)-2-[[(1,1-dimethyletoxy)carbonyl]amino]-5-[[imino(nitroamino)methyl]amino]-1-oxopentyl]-4-methylpiperidine-2-carboxylate diastereoisomers ( 6) as olio (ratio 97.7/2.3). [0075] HPLC purity area as the sum of the two diastereoisomers: 98.2%. The product was used partly as it is in the subsequent step.
  • 27
  • [ 2188-18-3 ]
  • [ 74892-82-3 ]
  • ethyl (2R,4R)-1-[(2S)-2-amino-5-[[imino(nitroamino)methyl]amino]-1-oxopentyl]-4-methylpiperidine-2-carboxylate dihydrochloride [ No CAS ]
  • 28
  • [ 131278-84-7 ]
  • [ 74892-82-3 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate; In water; ethyl acetate; at 15 - 20℃; for 1h; 74 g of a mixture of ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate L-tartrate (13) and ethyl (2S,4S)-4-methyl-2-piperidinecarboxylate L-tartrate (14) (ratio 97/3), 370 ml of ethyl acetate and 75 ml of water are introduced in a reactor. Cooling is carried out at 15 C. and an aqueous solution (150 ml) of potassium carbonate (35 g) is added. The obtained biphasic solution is left under stirring at 20 C. for 1 hour, then the phases are separated, the aqueous phase is extracted once again using 150 ml of ethyl acetate, the two organic phases are concentrated by distillation at reduced pressure obtaining 36 g of ester, with a 96.05% potentiometric titre 96.05% then 34.4 g at 100%, with a 99.9% chemical purity. Molar yield: 88%. Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate (9)/ethyl (2S,4S)-4-methyl-2-piperidinecarboxylate (10) (97.7/2.3) ratio.
  • 29
  • ethyl 4-methyl-2-piperidinecarboxylate L-tartrate [ No CAS ]
  • [ 74892-82-3 ]
  • [ 78306-52-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In water; ethyl acetate; at 15 - 20℃; for 1.08333h; 65 g of a mixture of ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate L-tartrate (13) and ethyl (2S,4S)-4-methyl-2-piperidinecarboxylate L-tartrate (14) (ratio 86/14), obtained in step 4A, 325 ml of ethyl acetate and 65 ml of water are introduced in a reactor. Cooling is carried out at 15 C. and an aqueous solution (130 ml) of potassium carbonate (31 g) is added in 5 minutes. The obtained biphasic solution is left under stirring at 20 C. for 1 hour, then the phases are separated, the aqueous phase is extracted once again using 130 ml of ethyl acetate, the two organic phases are concentrated by distillation at reduced pressure obtaining 29.4 g of ester (at 100%), with a 99.9% chemical purity. Molar yield 85%. Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate (9)/ethyl (2S,4S)-4-methyl-2-piperidinecarboxylate (10) (87/13) ratio.
  • 30
  • ethyl trans-(±)-4-methylpiperidine-2-carboxylate [ No CAS ]
  • [ 74892-82-3 ]
  • 31
  • trans-(±)-4-methylpiperidine-2-carboxylic acid hydrochloride [ No CAS ]
  • [ 74892-82-3 ]
  • 32
  • [ 153886-63-6 ]
  • N-Boc-N'-nitro-L-arginine [ No CAS ]
  • [ 74892-82-3 ]
  • (2R,4R)-1-[NG-nitro-N2-(3-methyl-8-quinolinesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.5% 35kg of chloroform,Add to the 50L reactor,0.2 kg of CDMT (2-chloro-4,6-dimethoxy-1,3,5-triazine) and 4 kg of NMM (N-methylmorpholine) were added to the reaction vessel.2kg of N-Boc-N'-nitro-L-arginine,Cool down to -30 C,After stirring to fully dissolve it,Add 3 kg of <strong>[74892-82-3](2R,4R)-4-methyl-2-piperidinecarboxylic acid ethyl ester</strong> and stir for 2 hours.TLC detection reaction is completed,Add 3kg of 3-methyl-8-quinolinesulfonyl chloride,Keep at room temperature for 3 hours,TLC detection reaction is completed,Add 10% baking soda solution to neutralize,Layered,dry,The organic phase is washed to neutral,Dry over anhydrous sodium sulfate,Distilling the solvent under reduced pressure,Obtaining a white solid product,94.5%,The yield was 87.5%.
  • 33
  • N2-(3-methyl-8-quinolinesulfonyl)-NG-nitro-L-arginine [ No CAS ]
  • [ 74892-82-3 ]
  • (2R,4R)-1-[NG-nitro-N2-(3-methyl-8-quinolinesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.6% 35kg of tetrahydrofuran,Add to the 50L reactor,2kg of N2-(3-methyl-8-quinolinesulfonyl)-NG-nitro-L-arginine was added.After warming up and refluxing,Cool down to -30 C,Keep 2 kg of phosphorus oxychloride at this temperature.Stir for 2 hours with heat.TLC test,The material points disappear,Then add 1.5 kg of <strong>[74892-82-3]ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate</strong> at this temperature.Stir for 2 hours with heat.TLC detects the reaction completely,Layered with saturated brine,The organic phase is concentrated under reduced pressure to an oil.Add saturated NaHCO3 solution and 35 kg of dichloromethane,Layered,The organic phase is washed to neutral,Dry over anhydrous sodium sulfate,Distilling the solvent under reduced pressure,Obtaining a yellow oily product,The content is 81.5%,The yield was 72.6%.
  • 34
  • [ 372-75-8 ]
  • [ 74892-82-3 ]
  • C15H28N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃;Cooling with ice; In a 250 ml three-neck round bottom flask,Add 10.00g (57.08mmol) of L-citrulline,9.78 g (57.08 mmol) of 2R, 4R-piperidinecarboxylic acid ethyl ester and 100 ml of tetrahydrofuran,Add 13.13g (68.49mmol) EDCI in an ice water bath,After finishing, continue stirring for 1-2 hours and minutes.The temperature was raised to room temperature, and stirring was continued for 3 to 4 hours until no starting point was observed (the reaction was followed by thin layer chromatography (TLC) or high performance liquid phase (HPLC)).After the reaction is completed, 5 ml of purified water is added to the system.The reaction was quenched and stirred for 20 minutes.The reaction solution was distilled under reduced pressure at 45 C to remove the solvent.Then dry with an oil pump until solvent-free.
  • 35
  • [ 74892-82-3 ]
  • C25H35N5O6S [ No CAS ]
 

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