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[ CAS No. 951163-61-4 ] {[proInfo.proName]}

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Chemical Structure| 951163-61-4
Chemical Structure| 951163-61-4
Structure of 951163-61-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 951163-61-4 ]

CAS No. :951163-61-4 MDL No. :MFCD11112079
Formula : C11H22N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 214.30 Pubchem ID :-
Synonyms :

Safety of [ 951163-61-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 951163-61-4 ]

* 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 [ 951163-61-4 ]

[ 951163-61-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 951163-61-4 ]
  • [ 112811-72-0 ]
  • 7-[3S-amino-5S-methylpiperidinyl]-1-cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-4-oxo-3-quinolinecarboxylic acid hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
[1-CYCLOPROPYL-1,] 4-dihydro-6,7-difluoro-8-methoxy-4-oxo-quinoline-3-carboxylic acid (Precursor A) (0.059 g, 0.200 mmol), (5 (S) -methyl-piperidin-3 (S) -yl)-carbamic acid tert-butyl ester (Precursor [M) _ (0.] 048 g, 0.210 mmol) and triethylamine (0.075 [ML)] are dissolved in N- methyl-pyrrolidone (2 mL). The reaction mixture is stirred at [80C] for 5 hours, then is poured on an ice/water mixture. The pH is lowered to 2 with diluted [HC1] and the resulting precipitate is filtered. The solid is then suspended in ethanol and 6N [HC1] is added. After 18 hours at room temperature, the desired final product is collected by filtration.
  • 2
  • [ 59279-60-6 ]
  • [ 74-88-4 ]
  • [ 951163-61-4 ]
YieldReaction ConditionsOperation in experiment
Example 7 One-pot synthesis of (3S,55)-3-(tent-butoxycarbonylamino)-5-methylpiperidine oxalate (compound 6b·0.5 H2C2O4) LiHMDS solution (520 mL of 1 M in THF) was charged into a one-liter four-necked flask at -78 C. under nitrogen. To this solution was added dropwise at <-60 C. a solution of crude Compound 2b (60.0 g in 300 mL of dry THF). The reaction mixture was stirred for 1.5 h at -78 C. MeI (44.4 g in 20 mL dry THF) was added. After stirring for 2 h at -70 C., diisopropylamine (30.0 g) was added to quench unreacted MeI. The mixture was stirred at -70 C. for 2.5 h. To the solution was added dropwise cold DIBALH (600 mL, 1 M in toluene) at such a rate that the solution temperature remained <-60 C. (~one hour period). After stirring for 0.5 h at -70 C., ammonia aqueous solution (360 mL, 30%) was added to the mixture within a five-minute period. The reaction temperature was allowed to rise to -40 C., ammonia gas (~70-80 g) was introduced, followed by addition of NaBH4 (12.0 g). After stirring at -10 C. for 10 hours, the reaction temperature was allowed to further rise to room temperature during a six-hour period while monitored by LC/MS. The released ammonia was trapped by ice water. 20% NaOH aqueous solution (400 mL) was added with stirring. The mixture was filtered through alumina gel in a sintered glass funnel with suction. The organic layer of the filtrate was washed with water (300 mL*2), and evaporated under vacuum to give crude compound 6b (16.4 g). The alumina gel was thoroughly washed with methanol and filtered with suction. The filtrate was evaporated under vacuum. The residue was then filtered through Celite and washed with ethyl acetate. The filtrate was concentrated under vacuum to give crude compound 6b (5.0 g). To determine the optical purity of compound 6b, its optical antipode (i.e. (3R,5R)) was synthesized in the same manner as those described in Examples 1-7 except D-glutamic acid was used instead of L-glutamic acid. Both compound 6b and its optical antipode were derivatized with (S)-(+)-1-(1-naphthyl)ethyl isocyanate, and the resulting chiral ureas were subjected to HPLC analysis. The results showed that compound 6b had an optical purity greater than 98%.
  • 3
  • [ 59279-60-6 ]
  • [ 951163-61-4 ]
YieldReaction ConditionsOperation in experiment
Example 5One-pot synthesis of (3S,55)-3-(tert-butoxycarbonylamino)-5-methylpiperidine (compound 6b)A solution of the crude compound 2b (16.0 g) in toluene (240 mL) was cooled to -78 C. with stirring under nitrogen. To the solution was added dropwise cold DIBALH (160 mL, 1 M in toluene) at such a rate that the solution temperature remained at <-60 C. After stirring for 1 hour at -78 C., ammonia aqueous solution (50 mL, 30%) and acetic acid (1.7 g) were added. The cooling bath was replaced with an ice bath and the reaction mixture was stirred at 0-5 C. for 1.5 hours. NaBH4 (1.1 g) was added and the reaction was monitored by LC/MS. After 1 h, additional NaBH4 (0.5 g) was added. The ice bath was removed and the reaction was stirred at room temperature for 18 hours. Celite (45 g) was added with stirring. The mixture was heated to 50 C. to remove ammonia and filtered through Celite-alumina gel in a sintered glass funnel with suction. The filtrate was subjected to extraction with 10% KHSO4 aqueous solution (80 mL×2). The Celite-alumina gel was rinsed 3 times with 185 mL of 1/10 (v/v) methanol/ethyl acetate for more than 10 minutes and then filtered with suction. The combined filtrates were subjected to extraction with 10% KHSO4 aqueous solution (100 mL x 2). All of the KHSO4 extracts were combined, washed with toluene (50 mL×2), neutralized with ammonia, and extracted with ethyl acetate (200 mL×3). The combined organic layers were evaporated under vacuum to give crude compound 6b (7.3 g, 61%). An analytical sample was prepared by silica gel column chromatography purification using 1/10/0.05 (v/v/v) methanol/ethyl acetate/ammonia water and followed by crystallization from hexane to give compound 6b as pale yellow granular crystal. Mp: 63-64 C. (hexane); 1H NMR (CDCl3, 300 MHz): delta 0.80 (d, J=6.6 Hz, 3H), 1.14 (ddd, 1H), 1.40 (s, 9H), 1.58 (ddd, 1H), 1.95 (dd, 1H), 2.16 (m, 1H), 2.65 (dd, 1H), 2.82 (dd, 1H), 2.90 (dd,1H), 3.70 (m, 1H), 5.41 (m,1H); MS: m/e 215.2 (M++1).Compound 6b was also prepared in the scales of 50 gram and 100 gram in the manners similar to that described above.Resolution of compound 6b was achieved by converting it to the salt form followed by crystallization or trituration using appropriate solvent systems. Table 1 below shows that resolution with various acids and recyrstalliaztion/trituration with various solvents afford high diastereomeric excess (de) values. TABLE 1 Purification of compound 6b in salt formation de value Resolving (%), Yield de value acid (0.5 Solvent crude (free (%), Entry molar eq.) system Method 6b base) pure 6b 1 d-tartaric acetone/ recrystallization 95 69 99.8 acid water 18/1 (v/v) 2 di-o- acetone recrystallization 95 78 98.8 toluoyl-d- tartaric acid 3 oxalic i-PrOH/ recrystallization 95 70 98.2 acid water 10/1 (v/v) 4 oxalic acetone hot trituration 97.5 71 99.0 acid 5 oxalic acetone/ hot trituration 97.5 73 >99.9 acid water 20/1 (v/v)
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