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Chemical Structure| 138163-08-3
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Product Details of [ 138163-08-3 ]

CAS No. :138163-08-3 MDL No. :MFCD01317806
Formula : C14H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZJQMLJFHCKTCSF-UHFFFAOYSA-N
M.W : 247.29 Pubchem ID :2776272
Synonyms :

Calculated chemistry of [ 138163-08-3 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.63
TPSA : 46.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 1.7
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 1.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.29
Solubility : 1.28 mg/ml ; 0.00518 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 1.67 mg/ml ; 0.00677 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.285 mg/ml ; 0.00115 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.52

Safety of [ 138163-08-3 ]

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 [ 138163-08-3 ]

* 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.

  • Upstream synthesis route of [ 138163-08-3 ]
  • Downstream synthetic route of [ 138163-08-3 ]

[ 138163-08-3 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 10314-99-5 ]
  • [ 498-94-2 ]
  • [ 138163-08-3 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 32, p. 10983 - 10992
  • 2
  • [ 2033-24-1 ]
  • [ 138163-08-3 ]
  • [ 63845-33-0 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 38, p. 4972 - 4974
  • 3
  • [ 122860-33-7 ]
  • [ 138163-08-3 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78 - -55℃; for 0.5 h;
Stage #2: With triethylamine In dichloromethane at -78 - 20℃;
Example 3; 4-Formyl-piperidine-1-carboxylic acid benzyl ester (3); Oxalyl chloride (59.1 ml_, 674 mmol) was dissolved in dichloromethane (500 ml_) and cooled to -78°C. Dimethylsulfoxide (68.3 ml_, 963 mmol) was added and the mixture was stirred for 15 min. 4-Hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (2) (120 g, 481 mmol) dissolved in dichloromethane (500 ml_) was added. The mixture was allowed to warm to -55°C for 15 min. The mixture was again cooled to -78°C and triethylamine (205 ml_, 1443 mmol) in dichloromethane (250 ml_) was added. The suspension was allowed to warm to room temperature and quenched with glacial acetic acid (100 ml_). The solution was washed with water and the aqueous phase extracted with dichloromethane (2 x 200 ml_). The combined organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated to give 4- formyl-piperidine-1-carboxylic acid benzyl ester (119 g, 100percent).
93%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5 h;
Stage #2: at -78℃; for 0.5 h;
To oxalyl chloride (10.3 mL, 0.120 mol) in 150 mL of DCM and at -78 °C, a solution of DMSO (17.1 mL, 0.241 mol) in DCM (25 mL) was added dropwisely. After 30 min, benzyl 4- (hydroxymethyl)-piperidine-l-carboxylate (20 g, 0.080 mol) in DCM (25 mL) was added dropwisely. After 30 min, Et3N (44.7 mL, 0.321 mol) was added. The resulting solution was stirred for 30 min at -78 °C. The reaction was diluted with water, extracted with DCM (3 x). Combined organic layers were washed with water (3 x 500 mL), dried over Na2S04, filtered and concentrated to give Intermediate 6C (18.5 g, 93.0percent). MS (ESI) m/z 247 (M+H)+.
75% With pyridinium chlorochromate In dichloromethane at 20℃; for 3 h; Example 25;. N-Benzyloxycarbonyl-4- (formyl)-piperidine (E-13).; A stirred suspension of N-(benzyloxycarbonyl)-4-hydroxymethyl)-piperidine (E-12,2 g, 8 mmol) and CeliteTM (4 g) in dry DCM (120 mL) at room temperature was treated with pyridinium chlorochromate (3.5 g, 16.0 mmol), stirred for 3 hours, and filtered on Celte. The filtrate was evaporated to a dark residue which was purified by column chromatography using a gradient of 25 to 50 percent EtOAc in hexane as eluant to give 1.5 g (75 percent) of aldehyde E-13 as a clear oil which was immediately used in the next step : 1H NMR (CDC13) 8 1.43 (dd, 2H, J=10), 1.78 (m, 2H), 2.31 (m, 1H), 2.91 (t, 2H, J=10. 6), 3.96 (m, 2H), 5.05 (s, 2H), 7.24 (m, 5H), 9.52 (s, 1H).
6.2 g With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 12 h; Reaction Step 2
Synthesis of benzyl 4-formylpiperidine-1-carboxylate
To a stirred solution of benzyl 4-(hydroxymethyl)piperidine-1-carboxylate (10.0 g, 40.2 mmol, 1.0 eq) in dichloromethane (150 ml), Dess-Martin periodinane (20.4 g, 48.2 mmol, 1.2 eq) was added at 0° C. and stirring was continued at room temperature for 12 h.
After completion of the reaction (monitored by TLC, 30percent ethyl acetate-hexane, Rf=0.45), the mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate solution, followed by brine.
The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure.
The crude product was purified by column chromatography on silica gel (100-200 mesh), eluting with a 30-40percent gradient of ethyl acetate in hexanes to obtain benzyl 4-formylpiperidine-1-carboxylate (6.2 g, 62.5percent). LCMS Purity: 78.54percent (ES+): m/z 248.27 (M+H+); tr=3.01 min.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2663 - 2666
[2] Patent: WO2007/93603, 2007, A1, . Location in patent: Page/Page column 15
[3] Patent: WO2014/22349, 2014, A1, . Location in patent: Paragraph 00158
[4] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 661 - 664
[5] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9830 - 9836
[6] Patent: WO2005/80394, 2005, A1, . Location in patent: Page/Page column 131-132
[7] European Journal of Organic Chemistry, 2008, # 25, p. 4277 - 4295
[8] Tetrahedron Letters, 2007, vol. 48, # 2, p. 199 - 202
[9] Patent: WO2014/70976, 2014, A1, . Location in patent: Page/Page column 20; 21
[10] Patent: US2015/252022, 2015, A1, . Location in patent: Paragraph 0375
[11] Patent: US2016/24056, 2016, A1, . Location in patent: Paragraph 0244
  • 4
  • [ 138163-07-2 ]
  • [ 138163-08-3 ]
YieldReaction ConditionsOperation in experiment
49% With diisobutylaluminium hydride In toluene at -78℃; Inert atmosphere Stage (iii):
Benzyl 4-formylpiperidine-1-carboxylate
A solution of 1-benzyl 4-methyl piperidine-1,4-dicarboxylate (10 g) in toluene (100 ml) under nitrogen was cooled to -78° C. DIBAL-H (60.9 ml) subsequently was added dropwise at -78° C., and the mixture was stirred at this temperature for 1 h (TLC control).
Because the reaction was incomplete, a further 0.2 eq of DIBAL-H was added and the mixture was stirred for a further 30 min (TLC control: some educt and the corresponding alcohol were to be detected).
Methanol (40 ml), followed by sat. sodium chloride solution (40 ml) were added slowly to the reaction mixture at -78° C.
The mixture was filtered over Celite and the solvent was removed in vacuo.
The residue was extracted with ethyl acetate (3*75 ml) and the extract was dried (Na2SO4) and concentrated in vacuo.
The crude product obtained in this way was purified by column chromatography (silica gel, 20percent ethyl acetate/hexane). Yield: 4.3 g (49percent)
49% With diisobutylaluminium hydride In toluene at -78℃; Inert atmosphere Stage (iii):
Benzyl 4-formylpiperidine-1-carboxylate
A solution of 1-benzyl 4-methylpiperidine-1,4-dicarboxylate (10 g) in toluene (100 ml) under nitrogen was cooled to -78° C. DIBAL-H (60.9 ml) was then added dropwise at -78° C., and the mixture was stirred for one hour at that temperature (TLC monitoring).
Because the reaction was incomplete, a further 0.2 eq. of DIBAL-H were added and stirring was carried out for a further 30 minutes (TLC monitoring: some starting material and the corresponding alcohol were detectable).
Methanol (40 ml) followed by saturated sodium chloride solution (40 ml) were added slowly to the reaction mixture at -78° C.
The mixture was filtered over Celite and the solvent was removed in vacuo.
The residue was extracted with ethyl acetate (3*75 ml), dried (Na2SO4) and concentrated in vacuo.
The crude product so obtained was purified by column chromatography (silica gel, 20percent ethyl acetate/hexane). Yield: 4.3 g (49percent)
49% With diisobutylaluminium hydride In toluene at -78℃; Inert atmosphere A solution of 1-benzyl 4-methylpiperidine-1,4-dicarboxylate (10 g) in toluene (100 ml), under nitrogen, was cooled to -78° C. Then DIBAL-H (60.9 ml) was added dropwise at -78° C., and the mixture was stirred for 1 h at that temperature (TLC monitoring). Because the reaction was incomplete, a further 0.2 eq. of DIBAL-H was added and stirring was carried out for a further 30 min (TLC monitoring: some starting material and the corresponding alcohol were detectable). Methanol (40 ml) followed by sat. sodium chloride solution (40 ml) were added slowly to the reaction mixture at -78° C. The mixture was filtered over celite, and the solvent was removed under vacuum. The residue was extracted with ethyl acetate (3.x.75 ml), dried (Na2SO4) and concentrated under vacuum. The crude product so obtained was purified by column chromatography (silica gel, 20percent ethyl acetate/hexane). Yield: 4.3 g (49percent)
49% With diisobutylaluminium hydride In toluene at -78℃; Inert atmosphere A solution of 1-benzyl-4-methyl piperidine-1,4-dicarboxylate (10 g) in toluene (100 ml) under nitrogen was cooled to -78° C. DIBAL-H (60.9 ml) was then added dropwise at -78° C. and the mixture was stirred for 1 h at that temperature (TLC monitoring). Because the conversion was incomplete, a further 0.2 eq. of DIBAL-H was added and stirring was carried out for a further 30 min. (TLC monitoring: some starting material and the corresponding alcohol were detectable). Methanol (40 ml) followed by sat. sodium chloride solution (40 ml) were added slowly to the reaction mixture at -78° C. The mixture was filtered over Celite and the solvent was removed in vacuo. The residue was extracted with ethyl acetate (3.x.75 ml), dried (Na2SO4) and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, 20percent ethyl acetate/hexane). Yield: 4.3 g (49percent)
49%
Stage #1: With diisobutylaluminium hydride In toluene at -78℃; Inert atmosphere
Stage #2: With methanol; water; sodium chloride In toluene at -78℃; Inert atmosphere
Step (iii):
Benzyl 4-formylpiperidine-1-carboxylate
A solution of 1-benzyl 4-methyl piperidine-1,4-dicarboxylate (10 g) in toluene (100 ml) under nitrogen was cooled to -78° C. DIBAL-H (60.9 ml) was then added dropwise at -78° C. and the mixture was stirred at this temperature for 1 h (TLC control).
Because the reaction was incomplete, a further 0.2 eq. of DIBAL-H was added and the mixture was stirred for a further 30 min (TLC control: some educt and the corresponding alcohol were to be detected).
Methanol (40 ml), followed by sat. sodium chloride solution (40 ml) were added slowly to the reaction mixture at -78° C.
The mixture was filtered over Celite and the solvent was removed in vacuo.
The residue was extracted with ethyl acetate (3*75 ml) and the extract was dried (Na2SO4) and concentrated in vacuo.
The crude product obtained in this way was purified by column chromatography (silica gel, 20percent ethyl acetate/hexane). Yield: 4.3 g (49percent)
49%
Stage #1: With diisobutylaluminium hydride In toluene at -78℃; for 1.5 h; Inert atmosphere
Stage #2: With methanol In toluene at -78℃;
Stage (iii): Benzyl 4-formylpiperidine-1-carboxylate; A solution of 1 -benzyl 4-methyl piperidine-1 ,4-dicarboxylate (10 g) in toluene (100 ml) under nitrogen was cooled to -78 0C. DIBAL-H (60.9 ml) was then added dropwise at -78 0C and the mixture was stirred at this temperature for 1 h (TLC control). Because the reaction was incomplete, a further 0.2 eq. of DIBAL-H was added and the mixture was stirred for a further 30 min (TLC control: some educt and the corresponding alcohol were to be detected). Methanol (40 ml), followed by sat. sodium chloride solution (40 ml) were added slowly to the reaction mixture at -78 0C. The mixture was filtered over Celite and the solvent was removed in vacuo. The residue was extracted with ethyl acetate (3 x 75 ml) and the extract was dried (Na2SO4) and concentrated in vacuo. The crude product obtained in this way was purified by column chromatography (silica gel, 20percent ethyl acetate / hexane). Yield: 4.3 g (49 percent)

Reference: [1] European Journal of Medicinal Chemistry, 1991, vol. 26, # 6, p. 625 - 631
[2] Patent: US2010/152158, 2010, A1, . Location in patent: Page/Page column 31
[3] Patent: US2010/173889, 2010, A1, . Location in patent: Page/Page column 60
[4] Patent: US2010/222324, 2010, A1, . Location in patent: Page/Page column 57
[5] Patent: US2010/234340, 2010, A1, . Location in patent: Page/Page column 41
[6] Patent: US2010/249095, 2010, A1, . Location in patent: Page/Page column 120
[7] Patent: WO2010/142402, 2010, A1, . Location in patent: Page/Page column 143
[8] Patent: US2003/13720, 2003, A1,
  • 5
  • [ 160809-38-1 ]
  • [ 138163-08-3 ]
YieldReaction ConditionsOperation in experiment
53% With diisobutylaluminium hydride In dichloromethane at -78℃; for 0.5 h; Add diisobutyl aluminum hydride (1 M in toluene, 30 [ML,] 30 mmol) over 5 minutes to a solution of 1- (benzyloxycarbonyl)-4- (ethoxycarbonyl) piperidine (7 g, 24 mmol) in anhydrous dichloromethane (150 mL) at-78°C under a nitrogen atmosphere. Stir the reaction mixture at this temperature for 30 minutes and then add 10percent aqueous sodium tartarate (100 [ML)] followed by dichloromethane. Stir the reaction mixture at room temperature overnight. Separate the phases and extract the aqueous phase with dichloromethane. Wash the combined organic phases sequentially with 10percent aqueous sodium tartarate, water, and saturated aqueous sodium chloride. Dry over sodium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 3: 1 hexanes: ethyl acetate to provide 3.15 g [(53percent)] of the title compound.
Reference: [1] Patent: WO2004/14900, 2004, A1, . Location in patent: Page 48-49
[2] Tetrahedron Letters, 2007, vol. 48, # 2, p. 199 - 202
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2663 - 2666
  • 6
  • [ 148148-48-5 ]
  • [ 138163-08-3 ]
YieldReaction ConditionsOperation in experiment
100% With lithium aluminium tetrahydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0℃; for 1 h; To a solution of isonipecotic acid (1.29g, 10 mmol) in a mixture of CH3CN/H2O (2:3, 0.1M), NaHCO3 (1.5eq) and Na2CO3 (1.5 eq) were added (pH~ 10-11). Once the mixture was cooled to 0 °C, Cbz-Cl (1.42 mL,1.7 g, 10 mmol). was slowly added The resulting solution was stirred for 2 h at rt. After completion ofthe reaction, the mixture was acidified by dropwise addition of a 1 N HCl aqueous solution. Then, CH3CNwas removed by evaporation, followed by the extraction with EtOAc (3x). Finally the combined organicphase was washed with brine, dried over Na2SO4, and concentrated to afford the desired product inquantitative yield, which was used in the next reaction without further purification.
Reference: [1] Synlett, 2017, vol. 28, # 3, p. 376 - 380
  • 7
  • [ 10314-99-5 ]
  • [ 498-94-2 ]
  • [ 138163-08-3 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 32, p. 10983 - 10992
  • 8
  • [ 79-37-8 ]
  • [ 122860-33-7 ]
  • [ 138163-08-3 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane; dimethyl sulfoxide 26c.
Phenylmethyl 4-formylpiperidinecarboxylate
To a stirred solution of oxalyl chloride (2M solution in dichloromethane, 10.9 mL, 21.9 mmol) was added DMSO (3.1 mL, 3.4 g, 43.8 mmol) in dichloromethane (6 mL) over a period of 15 minutes.
The product of Example 26b (4.4 g, 17.5 mmol) in dichloromethane (7 mL) was then added at -78° C. over a period of 15 minutes.
The resultant solution was stirred at -78° C. for 1 hour and then triethylamine (12.2 mL, 8.86 g, 87.5 mmol) was added, dropwise, over a period of 15minutes.
The mixture was further stirred at -78° C. for 30 min and then at 0° C. for 15 min.
The reaction mixture was quenched with water and extracted with dichloromethane.
The combined organic phase was washed with 1percent HCl, water, dried over sodium sulfate, filtered and evaporated to give the title compound (4.4 g, 100percent) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ9.65 (s, 1H), 7.28-7.38 (m, 5H), 5.12 (s, 2H), 4.04 (br d, J=13.1 Hz, 2H), 2.97-3.06 (m, 2H), 2.38-2.45 (m, 1H), 1.88-1.92 (m,2H), 1.52-1.64 (m, 2H).
13C NMR (75 MHz, CDCl3) δ202.7, 155.2, 136.7, 128.5, 128.6, 127.9, 67.2, 47.8, 43.0, 25.1. LRMS (APIMS) m/z 248 (MH+).
Reference: [1] Patent: US2003/203915, 2003, A1,
  • 9
  • [ 10314-98-4 ]
  • [ 138163-08-3 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 32, p. 10983 - 10992
[2] European Journal of Medicinal Chemistry, 1991, vol. 26, # 6, p. 625 - 631
[3] Patent: WO2006/21449, 2006, A1, . Location in patent: Page/Page column 7
[4] Synlett, 2017, vol. 28, # 3, p. 376 - 380
[5] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9830 - 9836
  • 10
  • [ 87413-09-0 ]
  • [ 122860-33-7 ]
  • [ 138163-08-3 ]
Reference: [1] Patent: US6265434, 2001, B1,
  • 11
  • [ 498-94-2 ]
  • [ 138163-08-3 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 32, p. 10983 - 10992
[2] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 661 - 664
[3] Synlett, 2017, vol. 28, # 3, p. 376 - 380
  • 12
  • [ 1126-09-6 ]
  • [ 138163-08-3 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 2, p. 199 - 202
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2663 - 2666
  • 13
  • [ 501-53-1 ]
  • [ 138163-08-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 19, p. 2663 - 2666
[2] Synlett, 2017, vol. 28, # 3, p. 376 - 380
  • 14
  • [ 6457-49-4 ]
  • [ 138163-08-3 ]
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 661 - 664
  • 15
  • [ 138163-08-3 ]
  • [ 161609-84-3 ]
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 23, p. 3758 - 3766
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