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[ CAS No. 216854-23-8 ] {[proInfo.proName]}

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Chemical Structure| 216854-23-8
Chemical Structure| 216854-23-8
Structure of 216854-23-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 216854-23-8 ]

CAS No. :216854-23-8 MDL No. :MFCD03093383
Formula : C10H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WUOQXNWMYLFAHT-QMMMGPOBSA-N
M.W : 200.28 Pubchem ID :1514171
Synonyms :
Chemical Name :(S)-tert-Butyl piperidin-3-ylcarbamate

Calculated chemistry of [ 216854-23-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 59.3
TPSA : 50.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.53
Log Po/w (XLOGP3) : 1.05
Log Po/w (WLOGP) : 0.88
Log Po/w (MLOGP) : 0.86
Log Po/w (SILICOS-IT) : 0.83
Consensus Log Po/w : 1.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.48
Solubility : 6.64 mg/ml ; 0.0332 mol/l
Class : Very soluble
Log S (Ali) : -1.7
Solubility : 4.01 mg/ml ; 0.02 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.05
Solubility : 1.8 mg/ml ; 0.00899 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.69

Safety of [ 216854-23-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 216854-23-8 ]

* 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 [ 216854-23-8 ]
  • Downstream synthetic route of [ 216854-23-8 ]

[ 216854-23-8 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
30% With borane-THF In tetrahydrofuran at 0 - 25℃; for 6.75 h; The product from Example 4 1 A (20.1 g, 94 mmol) in THF (250 mL) was treated with borane-THF complex (162 mL, 1M in THF, 162 mmol; Aldrich) dropwise over 45 minutes at 0 °C. After 1 hour, the cold bath was removed and the solution was stirred at 20-25 °C for 6 hours. The reaction mixture was quenched by cautious addition of methanol (100 mL) and 5percent NaHCO3 (300 mL). The mixture was stirred vigorously for 16 hours and then the volume was reduced under reduced pressure. The residue was treated with methanol (200 mL), warmed to reflux for 30 minutes, and concentrated under reduced pressure. This process was repeated twice more. The residue was suspended in 20percent K2CO3 (200 mL) and extracted with diethyl ether (3 x 200 mL). The combined extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (dichloromethane:methanol:NH4OH, 90:10:1) to provide the title compound as a white solid (5.64 g, 30percent). MS (CI/NH3) m/z 201 (M+H)+.
Reference: [1] Patent: EP1428824, 2004, A1, . Location in patent: Page 44
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Reference: [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
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Reference: [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
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Reference: [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
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  • [ 162955-48-8 ]
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Reference: [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
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  • [ 309962-63-8 ]
Reference: [1] Patent: WO2012/58645, 2012, A1,
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  • [ 501-53-1 ]
  • [ 216854-23-8 ]
  • [ 876379-22-5 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine In dichloromethane at 0 - 20℃; A 200 mL round bottom flask was charged with (S)-tert-butyl piperidin-3-ylcarbamate (2.02 g, 10.09 mmol). CH2Cl2 (40 mL) was added, followed by triethylamine (2.25 mL, 16.1 mmol). The colorless solution was cooled to 0 °C, and then benzyl chloroformate (1.70 mL, 11.9 mmol) was added dropwise. The resulting heterogeneous mixture was allowed to stir at 0 °C with slow warming to room temperature. After stirring overnight, the reaction was partitioned between CH2Cl2 and H2O. The aqueous layer was extracted with CH2Cl2, and the combined organics were washed with brine, dried (Na2SO4), filtered, and concentrated to give the title compound as a colorless, viscous oil that crystallized on standing in vacuo (3.35 g, 99percent).
95% With triethylamine In dichloromethane at 0℃; for 1 h; solution of tert-butyl N-[(3S)-piperidin-3-yl]carbamate (100 mg, 0.499 mmol) and triethylamine (0.104 ml, 0.749 mmol) in DCM (2.5 ml) was cooled to 0°C, followed by addition of benzyl chloroformate (0.101 ml, 0.599 mmol), and it was stirred for one hour. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane) to yield benzyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidine-1-carboxylate (159 mg, 95percent) as a colorless solid. LCMS: m/z 335 [M+H]+ HPLC retention time: 0.82 min (analysis condition F)
95% With triethylamine In ethyl acetate at 0℃; for 1 h; A solution of tert-butyl N-[(3S)-piperidin-3-yl]carbamate (100 mg, 0.499 mmol) and triethylamine (0.104 ml, 0.749 mmol) in DCM (2.5 ml) was cooled to 0°C, benzyl chloroformate (0.101 ml, 0.599 mmol) was added, and the mixture was stirred for one hour.
Water was added to the reaction mixture, then extraction with ethyl acetate was carried out.
The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate.
The drying agent was removed by filtration, then concentration under reduced pressure was carried out.
The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give benzyl (3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]piperidine-1-carboxylate (159 mg, 95percent) as a colorless solid.
LCMS: m/z 335 [M+H]+
89% With triethylamine In dichloromethane at 0 - 20℃; Example 47[0296] Synthesis of (,S')-2-(3,5-dichlorophenylamino)-l-(3-(ethyl(7H-pyrrolo[2,3- d]pyrimidin-4-yl)amino)piperidin- 1 -yl)ethanone: Reagents and conditions: a) Et3N, CH2C12, Cbz-Cl, 0 °C, 4 h; b) NaH, DMF, EtBr, rt, 4h; Dioxane.HCl, rt, 1 h; d) 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, DIEA, DMF, 100 °C, 4 e) 10percent Pd/C, H2, rt, 1 h; f) 2-(3,5-dichlorophenylamino)acetic acid, EDCI, HOBt, DIEA, DMF, rt, 15 h; g) K2C03, aq. MeOH, 60 °C, 1 h.[0297] Synthesis of (^-benzyl 3-(ieri-butoxycarbonylamino)piperidine-l-carboxylate:To a solution of (^-ieri-butyl piperidin-3-ylcarbamate (5 g, 24.9 mmol) and Et3N (3.8 mL, 27.4 mmol) in CH2C12 (75 mL) was added Cbz-Cl (3.92 mL, 27.4 mmol) at 0 °C, after the addition was complete the reaction was warmed to rt and stirred for 4 h. The reaction was diluted with ice cooled water (30 mL) and the CH2C12 layer was separated and dried over Na2S04 and concentrated in vacuo to give (7.5 g, 89percent) of the tilted compound. 1H NMR (400 MHz, CDC13): δ 7.40-7.24 (m, 5H), 5.18 (s, 2H), 4.58 (bs, 1H), 3.80-3.62 (m, 2H), 3.55-3.41 (m, 1H), 3.37-3.21 (m, 2H), 1.82-1.78 (m, 1H), 1.75-1.69 (m, 1H), 1.61-1.53 (m, 2H), 1.42 (s, 9H). ES-MS: m/z [M+l] = 335.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1690 - 1694
[2] Patent: EP2842939, 2015, A1, . Location in patent: Paragraph 1593
[3] Patent: EP2842946, 2015, A1, . Location in patent: Paragraph 1681
[4] Patent: WO2012/58645, 2012, A1, . Location in patent: Page/Page column 103-104
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1690 - 1694
[2] Patent: EP2842939, 2015, A1,
[3] Patent: EP2842946, 2015, A1,
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