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[ CAS No. 147081-49-0 ] {[proInfo.proName]}

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Chemical Structure| 147081-49-0
Chemical Structure| 147081-49-0
Structure of 147081-49-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 147081-49-0 ]

CAS No. :147081-49-0 MDL No. :MFCD03419272
Formula : C9H18N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 186.25 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 147081-49-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.49
TPSA : 55.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.24
Log Po/w (XLOGP3) : 0.37
Log Po/w (WLOGP) : 0.57
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 0.04
Consensus Log Po/w : 0.76

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.03
Solubility : 17.4 mg/ml ; 0.0934 mol/l
Class : Very soluble
Log S (Ali) : -1.1
Solubility : 14.7 mg/ml ; 0.0791 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.64
Solubility : 43.0 mg/ml ; 0.231 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 147081-49-0 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P210-P264-P270-P273-P280-P301+P310+P330-P305+P351+P338+P310-P370+P378-P403+P235-P405-P501 UN#:2922
Hazard Statements:H227-H301-H318-H401 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 147081-49-0 ]

* 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 [ 147081-49-0 ]
  • Downstream synthetic route of [ 147081-49-0 ]

[ 147081-49-0 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 186550-13-0 ]
  • [ 101385-93-7 ]
  • [ 147081-49-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 6, p. 807 - 812
  • 2
  • [ 143700-04-3 ]
  • [ 147081-49-0 ]
YieldReaction ConditionsOperation in experiment
96% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12 h; A mixture of (R) -tert-butyl 3-azidopyrrolidine-1-carboxylate (250 mg, 1.18 mmol) and Pd/C (10, 50 mg) in methanol (10 mL) was stirred at rt under H2 at atmospheric pressure for 12 h and filtered. The filtrate was concentrated to give (R) -tert-butyl 3-aminopyrrolidine-1-carboxylate as colorless liquid (210 mg, 96) .1H NMR (600 MHz, CDCl3) : δ ppm 3.39-3.49 (m, 3H) , 3.27-3.32 (m, 1H) , 2.95-3.03 (m, 1H) , 1.98-2.08 (m, 1H) , 1.63-1.70 (m, 1H) , 1.41 (s, 9H) and MS-ESI: m/z 131.20 [M-55] +.
96% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12 h; The compound (R) -3- azido-pyrrolidine-1-carboxylate (250mg, 1.18mmol) and Pd / C (10percent, 50mg) wasdissolved in methanol (10mL of), at room temperature, normal pressure hydrogen reduction, the reaction isstopped after 12h the reaction, filtration, and the filtrate was concentrated to give 210mg of colorless liquid: (R) -3- Amino-pyrrolidine-1-carboxylate, yield: 96percent.
93% With hydrogen In methanol at 20℃; for 6 h; To a solution of product 178 (907 mg, 4.27 mmol, 1.0 eq.) in 25 mL of methanol, palladium on charcoal (454 mg, 0.43 mmol, 0.1 eq.) is added. The reaction medium is submitted to hydrogenation at atmospheric pressure and at room temperature for 6 hours. The reaction medium is then filtered on celite and concentrated under dry conditions under reduced pressure. The expected compound is obtained as a yellow oil (740 mg, 93percent).
Reference: [1] Patent: WO2016/34134, 2016, A1, . Location in patent: Paragraph 00508
[2] Patent: CN105399698, 2016, A, . Location in patent: Paragraph 1493-1495
[3] Patent: US2009/221565, 2009, A1, . Location in patent: Page/Page column 50
[4] Advanced Synthesis and Catalysis, 2009, vol. 351, # 14-15, p. 2288 - 2294
[5] Tetrahedron, 2009, vol. 65, # 41, p. 8513 - 8523
  • 3
  • [ 945483-28-3 ]
  • [ 147081-49-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 12, p. 1961 - 1969
  • 4
  • [ 132945-75-6 ]
  • [ 147081-49-0 ]
YieldReaction ConditionsOperation in experiment
64% With ammonia In water at 80 - 90℃; for 10 - 19 h; Step 5-1: Production of (R)-1-(tert-butoxycarbonyl)-3-aminopyrrolidine; To 5.56 g of (S)-1-(tert-butoxycarbonyl)-3-(methanesulfonyloxy)pyrrolidine produced by the method described in Production Example 2 was added 36.4 g of a 28percent by weight aqueous ammonia solution, and the mixture was stirred at 90°C for 19 hrs (internal pressure: about 4 barr). After cooling, ammonia was removed by distillation, and thereto were added 10 ml of water and 3.21 g of a 30percent by weight aqueous sodium hydroxide solution. After the aqueous solution was concentrated under reduced pressure, 10 ml of a saturated brine was added thereto, and the target substance was extracted with 20 ml of ethyl acetate three times. Thus obtained organic layer was washed with 3 ml of a saturated brine, followed by concentration under reduced pressure to give the title compound as 3.20 g of a yellow liquid (chemical purity: 63.5 areapercent,, optical purity: 100percent e.e., yield: 64percent). It was ascertained that 41.4percent of the optically active 1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine represented by the above formula (3) was contaminated with respect to the HPLC area value of the title compound, while 7.8percent of 1-(tert-butoxycarbonyl)-3,4-dehydropyrrolidine represented by the above formula (4) was contaminated with respect to the HPLC area value of the title compound.; Step 6-1: Production of (R)-1-(tert-butoxycarbonyl)-3-aminopyrrolidine; To 11.2 g of a solution in toluene including 7.83 g of (S)-1-(tert-butoxycarbonyl)-3-(methanesulfonyloxy)pyrrolidine produced by the method described in Production Example 2 was added 62.7 g of a 40percent by weight aqueous ammonia solution, and the mixture was stirred at 80°C for 10 hrs (internal pressure: about 8 barr). After cooling, the reaction mixture was concentrated under reduced pressure, to which 31.3 g of a saturated brine, 19.6 g of toluene, and 4.13 g of a 30percent by weight aqueous sodium hydroxide solution were added. Thus obtained organic layer was concentrated under reduced pressure to give the title compound as 5.09 g of a yellow liquid (chemical purity: 74.5 areapercent, yield: 74percent, optical purity: 99.4percent ee). It was ascertained that 18.1percent of the optically active 1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine represented by the above formula (3) was contaminated with respect to the HPLC area value of the title compound, while 4.1percent of 1-(tert-butoxycarbonyl)-3,4-dehydropyrrolidine represented by the above formula (4) was contaminated with respect to the HPLC area value of the title compound.
Reference: [1] Patent: EP2050735, 2009, A1, . Location in patent: Page/Page column 19-20
  • 5
  • [ 1013-88-3 ]
  • [ 24424-99-5 ]
  • [ 116183-82-5 ]
  • [ 4248-19-5 ]
  • [ 147081-49-0 ]
Reference: [1] Patent: US2002/65270, 2002, A1,
[2] Patent: US2002/137747, 2002, A1,
[3] Patent: US6906067, 2005, B2,
  • 6
  • [ 24424-99-5 ]
  • [ 116183-82-5 ]
  • [ 147081-49-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 24, p. 6779 - 6784
  • 7
  • [ 186550-13-0 ]
  • [ 101385-93-7 ]
  • [ 147081-49-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 6, p. 807 - 812
  • 8
  • [ 1004538-27-5 ]
  • [ 147081-49-0 ]
Reference: [1] Patent: EP2050735, 2009, A1, . Location in patent: Page/Page column 20
  • 9
  • [ 101469-92-5 ]
  • [ 147081-49-0 ]
Reference: [1] Patent: WO2016/34134, 2016, A1,
[2] Patent: CN105399698, 2016, A,
  • 10
  • [ 50-00-0 ]
  • [ 147081-49-0 ]
  • [ 1004538-33-3 ]
Reference: [1] Patent: EP2607363, 2013, A1, . Location in patent: Paragraph 0130
  • 11
  • [ 147081-49-0 ]
  • [ 1004538-34-4 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In water; ethyl acetate at 0 - 22℃; for 1 h; Step 10-3: Production of (R)-1-(tert-butoxycarbonyl)-3-aminopyrrolidine hydrochloric acid salt; To 30 ml of a solution in isopropanol including 2.60 g of (R)-1-(tert-butoxycarbonyl)-3-aminopyrrolidine produced by the method described in the step 10-1 (chemical purity: 48.7 areapercent, optical purity: 96.6percent ee, contaminated with 48.4percent of the optically active 1-(tert-butoxycarbonyl)-3-methoxypyrrolidine represented by the above formula (9) with respect to the HPLC area value of the title compound, and with 31.9percent of 1-(tert-butoxycarbonyl)-3,4-dehydropyrrolidine represented by the above formula (10) with respect to the HPLC area value of the title compound) was added 1.39 g of conc. hydrochloric acid, and concentrated under reduced pressure. Thereto was added 50 ml of ethyl acetate, and stirred at 22°C for 30 min. After stirring for additional 30 min under cooling on ice, the crystal was filtrated under reduced pressure. The crystal was washed with 20 ml of ethyl acetate, and thereafter vacuum drying was carried out to give the title compound as 2.51 g of a white solid (chemical purity: 99.6 areapercent, yield: 95percent, optical purity: 99.7percent ee). It was ascertained that the optically active 1-(tert-butoxycarbonyl)-3-methoxypyrrolidine represented by the above formula (9), and the 1-(tert-butoxycarbonyl)-3,4-dehydropyrrolidine represented by the above formula (10) were not detected on HPLC.
Reference: [1] Patent: EP2050735, 2009, A1, . Location in patent: Page/Page column 22
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