[ CAS No. 362703-57-9 ] {[proInfo.proName]}

Name: 362703-57-9|tert-Butyl 4-amino-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate|98%
Brand: Ambeed
SKU: A640442
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Quality Control of [ 362703-57-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 362703-57-9 ]

CAS No. :	362703-57-9	MDL No. :	MFCD07784120
Formula :	C₁₃H₂₄N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UJWYRWKTHZQRLH-UHFFFAOYSA-N
M.W :	272.34	Pubchem ID :	25418816
Synonyms :

Calculated chemistry of [ 362703-57-9 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.85
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	75.04
TPSA :	81.86 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.02
Log Po/w (XLOGP3) :	0.92
Log Po/w (WLOGP) :	0.9
Log Po/w (MLOGP) :	0.77
Log Po/w (SILICOS-IT) :	0.71
Consensus Log Po/w :	1.26

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.71
Solubility :	5.28 mg/ml ; 0.0194 mol/l
Class :	Very soluble
Log S (Ali) :	-2.22
Solubility :	1.62 mg/ml ; 0.00596 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.61
Solubility :	6.61 mg/ml ; 0.0243 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 362703-57-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 362703-57-9 ]

* 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 [ 362703-57-9 ]

[ 362703-57-9 ] Synthesis Path-Downstream 1~47

1
[ 362703-57-9 ]
[ 362488-51-5 ]
[ 362703-58-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide

Reference： [1]Gilmore, John L.; King, Bryan W.; Harris, Cathy; Maduskuie, Thomas; Mercer, Stephen E.; Liu, Rui-Qin; Covington, Maryanne B.; Qian, Mingxin; Ribadeneria, Maria D.; Vaddi, Krishna; Trzaskos, James M.; Newton, Robert C.; Decicco, Carl P.; Duan, James J.-W. [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2699 - 2704]

2
[ 169206-65-9 ]
[ 362703-57-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With ammonia In ethanol at 12℃; for 80h; A stainless steel bomb reactor;	35.b A stainless steel bomb reactor containing a solution of the ester (19.6 g, 76.8 mmol) from reaction (35a) in ethanol (100 mL) was charged with ammonia (50 g). The reactor was heated at 80° C. for 12 h. After cooling to rt, the excess ammonia was allowed to evaporate. The solution was filtered through Celite and concentrated to give the desired amine (14.6 g, 70%). MS found: (M+H)+=273.
	With ammonia In methanol at 80℃;
	With ammonia In methanol at 100℃; for 16h; Autoclave;	2 Step 2 - Tert-butyl 4-amino-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate To tert-butyl 4-(2-methoxy-2-oxo-ethylidene)piperidine-1-carboxylate (1.00 g, 3.92 mmol) was added a solution of ammonia in methanol (4 M/L, 30.0 mL). The mixture was stirred at 100 °C for 16 hours under autoclave. On completion, the mixture was concentrated. The residue was purified by silica gel chromatography (petroleum ether /ethyl acetate = 10:1, dichloromethane / methanol = 10:1) to give the title compound. 1H NMR (400 MHz, CDCl3) δ = 3.69 (s, 3H), 3.61 (brs, 2H), 3.39 - 3.21 (m, 2H), 2.42 (s, 2H), 1.62 - 1.50 (m, 4H), 1.45 (s, 9H).

Reference： [1]Current Patent Assignee: Duan, Jingwu; King, Bryan W.; Decicco, Carl; Maduskuie JR., Thomas P.; Voss, Mathew E. - US2004/72802, 2004, A1 Location in patent: Page/Page column 49
[2]Gilmore, John L.; King, Bryan W.; Harris, Cathy; Maduskuie, Thomas; Mercer, Stephen E.; Liu, Rui-Qin; Covington, Maryanne B.; Qian, Mingxin; Ribadeneria, Maria D.; Vaddi, Krishna; Trzaskos, James M.; Newton, Robert C.; Decicco, Carl P.; Duan, James J.-W. [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2699 - 2704]
[3]Current Patent Assignee: RAZE THERAPEUTICS - WO2017/156177, 2017, A1 Location in patent: Paragraph 00352

3
[ 362703-57-9 ]
[ 362703-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane

4
[ 362703-57-9 ]
[ 362703-59-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂

5
[ 362703-57-9 ]
N-{4-[2-(hydroxyamino)-2-oxoethyl]-1-methyl-4-piperidinyl}-4-[-(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane 4: NH₂OH; KOH / methanol

6
[ 362703-57-9 ]
[ 362697-55-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: NH₂OH; KOH / methanol 3: TFA / CH₂Cl₂

7
[ 362703-57-9 ]
[ 362703-78-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane

8
[ 362703-57-9 ]
[ 362703-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide

9
[ 362703-57-9 ]
[ 362703-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane

10
[ 362703-57-9 ]
[ 362703-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide

11
[ 362703-57-9 ]
[ 362704-28-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane

12
[ 362703-57-9 ]
[ 362703-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide

13
[ 362703-57-9 ]
N-{1-ethyl-4-[2-(hydroxyamino)-2-oxoethyl]-4-piperidinyl}-4-[-(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane 4: NH₂OH; KOH / methanol

14
[ 362703-57-9 ]
[ 362703-70-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane

15
[ 362703-57-9 ]
[ 362703-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide

16
[ 362703-57-9 ]
N-[4-[2-(hydroxyamino)-2-oxoethyl]-1-(methylsulfonyl)-4-piperidinyl]-4-[(2-methyl-4-quinolinyl)methoxyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide 4: NH₂OH; KOH / methanol

17
[ 362703-57-9 ]
N-{1-acetyl-4-[2-(hydroxyamino)-2-oxoethyl]-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide 4: NH₂OH; KOH / methanol

18
[ 362703-57-9 ]
N-{4-[2-(hydroxyamino)-2-oxoethyl]-1-propyl-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane 4: NH₂OH; KOH / methanol

19
[ 362703-57-9 ]
[ 362703-63-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide

20
[ 362703-57-9 ]
N-{4-[2-(hydroxyamino)-2-oxoethyl]-1-propionyl-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide 4: NH₂OH; KOH / methanol

21
[ 362703-57-9 ]
[ 362704-20-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane

22
[ 362703-57-9 ]
[ 362703-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide

23
[ 362703-57-9 ]
[ 362704-10-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane

24
[ 362703-57-9 ]
N-{4-[2-(hydroxyamino)-2-oxoethyl]-1-neopentyl-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane 4: NH₂OH; KOH / methanol

25
[ 362703-57-9 ]
N-{4-[2-(hydroxyamino)-2-oxoethyl]-1-isobutyryl-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide 4: NH₂OH; KOH / methanol

26
[ 362703-57-9 ]
N-{1-(2-fluoroethyl)-4-[2-(hydroxyamino)-2-oxoethyl]-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane 4: NH₂OH; KOH / methanol

27
[ 362703-57-9 ]
N-{1-(2,2-dimethylpropanoyl)-4-[2-(hydroxyamino)-2-oxoethyl]-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide 4: NH₂OH; KOH / methanol

28
[ 362703-57-9 ]
[ 362703-87-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide

29
[ 362703-57-9 ]
[ 362697-53-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: NH₂OH; KOH / methanol

30
[ 362703-57-9 ]
N-{1-benzyl-4-[2-(hydroxyamino)-2-oxoethyl]-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane 4: NH₂OH; KOH / methanol

31
[ 362703-57-9 ]
N-[4-[2-(hydroxyamino)-2-oxoethyl]-1-(3-methylbutanoyl)-4-piperidinyl]-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide 4: NH₂OH; KOH / methanol

32
[ 362703-57-9 ]
[ 362704-22-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane

33
[ 362703-57-9 ]
N-{4-[2-(hydroxyamino)-2-oxoethyl]-1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane 4: NH₂OH; KOH / methanol

34
[ 362703-57-9 ]
N-{1-(3,3-dimethylbutanoyl)-4-[2-(hydroxyamino)-2-oxoethyl]-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: BOP; N-methylmorpholine / dimethylformamide 4: NH₂OH; KOH / methanol

35
[ 362703-57-9 ]
N-{1-[2-(ethylsulfonyl)ethyl]-4-[2-(hydroxyamino)-2-oxoethyl]-4-piperidinyl}-4-[(2-methyl-4-quinolinyl)methoxy]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: BOP; N-methylmorpholine / dimethylformamide 2: TFA / CH₂Cl₂ 3: NaBH(OAc)3 / 1,2-dichloro-ethane 4: NH₂OH; KOH / methanol

36
[ 79099-07-3 ]
[ 362703-57-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene / Heating 2: NH₃ / methanol / 80 °C
	Multi-step reaction with 2 steps 1: toluene / 16 h / 110 °C 2: ammonia / methanol / 16 h / 100 °C / Autoclave

Yield	Reaction Conditions	Operation in experiment
4.65 g	With ammonia In methanol at 90℃; for 96h; Sealed tube;	1.2 Synthesis of methyl (4-aminotetrahydro-2H-pyran-4-yl)acetate General procedure: (2) Synthesis of methyl (4-aminotetrahydro-2H-pyran-4-yl)acetate An 8 mol/L ammonia-methanol solution (100 mL) of the compound (13.6 g) obtained in step (1) above was stirred in a sealed tube at 90°C for 4 days. After being cooled to room temperature, the mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol = 100:0-90:10) to give methyl (4-aminotetrahydro-2H-pyran-4-yl)acetate as a yellow oil (7.09 g). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.44 - 1.56 (m, 2 H) 1.64 - 1.79 (m, 2 H) 2.45 (s, 2 H) 3.63 - 3.86 (m, 7 H). MS ESI/APCI Dual posi: 174[M+H]+, 196[M+Na]+.

38
[ 362703-57-9 ]
[ 1312784-58-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 1.33333h; Inert atmosphere;	128.A Step A: tert-butyl 4-amino-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (3.0 g, 11 mmol) was dissolved in tetrahydrofuran (30 mL, 11 mmol) in a 100 mL reaction flask charged with a stir bar. The solution was cooled to 0°C and placed under nitrogen. Lithium aluminum hydride (19 mL, 19 mmol) (1M in THF, anhydrous) was added dropwise over 20 minutes via addition funnel. The reaction was stirred from 0°C to RT for 1 hour. The reaction was cooled to 0°C and quenched with water (.72 μL) followed by 15% NaOH (.72 μL) then water (2.1 mL). The mixture was stirred at RT for 30 minutes. The crude solution was filtered through celite. The solids were washed with EtOAc and the filtrate was condensed to afford tert-butyl 4-amino-4-(2-hydroxyethyl)piperidine-1-carboxylate (1.8 g, 66% yield). m/z (esi/APCI) M+1 = 245.2.

Reference： [1]Current Patent Assignee: PFIZER INC; ARRAY BIOPHARMACEUTICAL - WO2020/81848, 2020, A1 Location in patent: Paragraph 00526

39
[ 362703-57-9 ]
tert-butyl 4-amino-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1.33 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 1 h / 20 °C