352004-58-1|3-(1-(tert-Butoxycarbonyl)piperidin-3-yl)propanoic acid| Ambeed

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Quality Control of [ 352004-58-1 ] Purity: 95% SDS Specification

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Product Details of [ 352004-58-1 ]

CAS No. :	352004-58-1
Formula :	C₁₃H₂₃NO₄
M.W :	257.33
SMILES Code :	O=C(O)CCC1CN(C(OC(C)(C)C)=O)CCC1
MDL No. :	MFCD02179008
InChI Key :	ZVYVZEUADCRFHK-UHFFFAOYSA-N
Pubchem ID :	2756824

Safety of [ 352004-58-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 352004-58-1 ]

* 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 [ 352004-58-1 ]

[ 352004-58-1 ] Synthesis Path-Downstream 1~15

1
[ 352004-58-1 ]
[ 1018505-37-7 ]
3-(2-{3-[(3,4-dimethoxyphenylcarbamoyl)methyl]phenylcarbamoyl}ethyl)piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;	3-Nitrophenylacetic acid (136 mg, 0.75 mmol), EDC (240 mg, 1.25 mmol) and HOBt (135 mg, 1 mmol) were combined in a reaction vial, and DMF (1 mL) was added, followed by N-methylmorpholine (0.137 mL, 1.25 mmol). The resulting solution was agitated for 1 h, after which time 3,4-dimethoxyaniline (115 mg, 0.75 mmol) was added and the reaction mixture was agitated overnight. The reaction mixture was then diluted with 6 mL dichloromethane, and the resulting mixture was washed with 1 N HCl (2 x 2 mL), NaHCO3 (satd. aq., 2x2 mL), and brine (1x2 mL), dried, and the solvents were evaporated to 216 mg of a dark oil. The product was purified by preparative HPLC using an acetonitrile/water/formic acid gradient to provide 36 mg (15% yield) of the intermediate N- (3,4-dimethoxy-phenyl)-2-(3-nitro-phenyl)-acetamide. This intermediate (36 mg, 0.114 mmol) was dissolved in methanol (1 mL) and ammonium formate (69 mg, 1.1 mmol) and then Pd/C (5 mg) was added. The reaction vial was sealed and heated to 45 0C overnight. The reaction mixture was filtered, and the mother liquors were diluted with ethyl acetate (10 mL). This mixture was washed with water (2 x 5 mL) and brine (1 x 5 mL), dried and concentrated to provide 10 mg (31% yield) of the desired intermediate 2-(3-amino- <n="109"/>phenyl)-JV-(3,4-dimethoxy-phenyl)-acetamide, which was used directly. Subsequently, 3- (2-carboxy-ethyl)-piperidine-l-carboxylic acid tert-butyl ester (12.9 mg, 0.05 mmol), EDC (11.5 mg, 0.06 mmol) and HOBt (8.1 mg, 0.06 mmol) were combined in a reaction vial, and DMF (1 mL) was added, followed by N-methylmorpholine (0.007 mL, 0.06 mmol). The resulting solution was agitated for 30 minutes, after which time the intermediate prepared above, 2-(3-amino-phenyl)-Λ/-(3,4-dimethoxy-phenyl)-acetamide (10 mg, 0.035 mmol) was added. The reaction mixture was agitated overnight, then diluted with 5 mL dichloromethane, and the resulting mixture was washed with IN HCl (2x2 mL), NaHCO3 (saturated aqueous, 1x2 mL), and brine (1x2 mL), dried, and concentrated to 19 mg (72%) of an amber oil, which was dissolved in dichloromethane (1 mL) and treated with SCX (136 mg, 0.12 mmol). The resulting mixture was agitated overnight. The reaction mixture was then filtered and the solids were washed with dichloromethane (2 x 2 mL) and methanol (2 x 2 mL). The product was eluted with NH3 in methanol (7 N, 2 x 2 mL), and the solvents were evaporated. The resulting residue was purified by preparative HPLC using an acetonitrile/water/formic acid gradient providing the title compound as a formate salt (6.5 mg, 38% yield), MS analysis electrospray, 426 (M+H).

References: [1]Patent: WO2008/86047,2008,A1 .Location in patent: Page/Page column 106-108.
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 759 - 777.

2
[ 352004-58-1 ]
3-(3-amino-phenyl)-N-(3,4-dimethoxy-phenyl)-propionamide TFA salt [ No CAS ]
[ 1038551-72-2 ]

Yield	Reaction Conditions	Operation in experiment
28%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20.0℃;	A reaction vial was charged with 3-(3-tert-butoxycarbonylamino-phenyl)-propionic acid (90 mg, 0.34 mmol), 3,4-dimethoxylaniline (90mg, 0.59mmol), EDC (100 mg, 0.64 mmol) and HOBt (100 mg, 0.74 mmol). DMF (2 mL) was added, followed by Hunig's base (0.3 mL, 1.72 mmol). The mixture was stirred at room temperature overnight, and then diluted with 10 mL water. The resulting mixture was extracted with 3 x 10 mL ethyl acetate. The organic layers were combined and washed with water and brine, dried with Na2SO4, and evaporated to give 150 mg crude {3-[2-(3,4-dimethoxy-phenylcarbamoyl)-ethyl]-phenyl}- carbamic acid tert-butyl ester which was used without purification. The ester intermediate was dissolved in dichloromethane (4 mL), and TFA (ImL) was added. The resulting mixture was stirred at room temperature for 2 h, then concentrated to provide the product, 3-(3-amino-phenyl)-Λ/-(3,4-dimethoxy-phenyl)-propionamide, as a TFA salt which was used without further purification (100 mg, 71% yield, 2 steps). This intermediate (lOOmg, 0.33 mmol) was then combined with 3-(2-carboxy-ethyl)-piperidine-l-carboxylic acid tert- butyl ester (100 mg, 0.39 mmol), EDC (100 mg, 0.64 mmol) and HOBt (100 mg, 0.74 mmol) in a reaction vial. DMF (2 mL) was added, followed by Hunig's base (0.3 mL, 1.72 <n="112"/>mmol). The mixture was stirred at room temperature overnight. The product was purified directly from the reaction mixture by preparative HPLC using an acetonitrile/water/formic acid gradient to afford the product, 3-(2-{3-[2-(3,4-dimethoxy-phenylcarbamoyl)-ethyl]- phenylcarbamoyl}-ethyl)-piperidine-l-carboxylic acid tert-butyl ester, as yellow oil (50 mg, 28% yield). This intermediate was then dissolved in dichloromethane (4 mL), and TFA (ImL) was added. The resulting mixture was stirred at room temperature for 2 hours then concentrated to provide the title compound as a TFA salt (27 mg, 66% yield); MS, electrospray, 440 (M+H).

References: [1]Patent: WO2008/86047,2008,A1 .Location in patent: Page/Page column 109-111.

3
[ 352004-58-1 ]
[ 1038549-47-1 ]
[ 1203719-56-5 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 759 - 777.

4
[ 352004-58-1 ]
[ 1038551-28-8 ]
[ 1203719-44-1 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 759 - 777.

5
[ 352004-58-1 ]
3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[(1-methyl-2(S)-azetidinyl)methoxy]pyridine [ No CAS ]

References: [1]Patent: US2013/184313,2013,A1 .

6
[ 352004-58-1 ]
3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[(1-methyl-2(S)-azetidinyl)methoxy]pyridine hydrochloride salt [ No CAS ]

References: [1]Patent: US2013/184313,2013,A1 .

7
[ 352004-58-1 ]
[ 553631-51-9 ]

References: [1]Patent: US2013/184313,2013,A1 .

8
[ 352004-58-1 ]
4-[2-(benzyloxy)ethyl]piperidine [ No CAS ]

References: [1]Patent: US2013/184313,2013,A1 .

9
[ 352004-58-1 ]
[ 1222139-94-7 ]

References: [1]Patent: US2013/184313,2013,A1 .

10
[ 352004-58-1 ]
3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[(2(S)-pyrrolidinyl)methoxy]pyridine hydrochloride [ No CAS ]

References: [1]Patent: US2013/184313,2013,A1 .
[2]Patent: US2013/184313,2013,A1 .

11
[ 352004-58-1 ]
3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]pyridine [ No CAS ]

References: [1]Patent: US2013/184313,2013,A1 .

12
[ 352004-58-1 ]
3-[(2(S)-azetidinyl)methoxy]-5-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]pyridine hydrochloride [ No CAS ]

References: [1]Patent: US2013/184313,2013,A1 .

13
[ 352004-58-1 ]
3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[2(R)-pyrrolidinylmethoxy]pyridine [ No CAS ]

References: [1]Patent: US2013/184313,2013,A1 .
[2]Patent: US2013/184313,2013,A1 .

14
[ 352004-58-1 ]
[ 163210-22-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With borane-THF; In tetrahydrofuran; at 20.0℃; for 16.0h;Inert atmosphere;	To a solution of commercially available <strong>[352004-58-1]3-[1-(tert-butoxycarbonyl)-3-piperidinyl]propionic acid</strong> (2.57 g, 10.0 mmol) in 100 mL of anhydrous THF was added slowly a solution of BH3.THF complex in THF (1.0 M, 20 mL, 2.0 equiv) at room temperature under N2. The solution was stirred for 16 h at room temperature. Water was added carefully (hydrogen evolution.), and the resulting solution was concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure to give the alcohol (2.35 g, 97%) as a colorless oil. LC-MS (ESI) m/z 244 (M+H+).

References: [1]Patent: US2013/184313,2013,A1 .Location in patent: Paragraph 1638.

15
[ 352004-58-1 ]
[ 1222139-94-7 ]
3-bromo-5-[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylmethoxy]pyridine [ No CAS ]

References: [1]Patent: US2013/184313,2013,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Arndt-Eistert Homologation • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Hunsdiecker-Borodin Reaction • Hydride Reductions • Lawesson's Reagent • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Reactions with Organometallic Reagents • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Related Functional Groups of
[ 352004-58-1 ]

Amides

A312891 [183483-09-2]

1-Boc-Piperidine-3-acetic acid

Similarity: 1.00

A650828 [941289-27-6]

(S)-2-(1-(tert-Butoxycarbonyl)piperidin-3-yl)acetic acid

Similarity: 1.00

A643336 [912940-89-7]

(R)-2-(1-(tert-Butoxycarbonyl)piperidin-3-yl)acetic acid

Similarity: 1.00

A592532 [1198466-23-7]

2-(3-(tert-Butoxycarbonyl)-3-azabicyclo[3.3.1]nonan-9-yl)acetic acid

Similarity: 1.00

A564719 [318536-95-7]

4-(1-(tert-Butoxycarbonyl)piperidin-3-yl)butanoic acid

Similarity: 1.00

Carboxylic Acids

A312891 [183483-09-2]

1-Boc-Piperidine-3-acetic acid

Similarity: 1.00

A650828 [941289-27-6]

(S)-2-(1-(tert-Butoxycarbonyl)piperidin-3-yl)acetic acid

Similarity: 1.00

A564719 [318536-95-7]

4-(1-(tert-Butoxycarbonyl)piperidin-3-yl)butanoic acid

Similarity: 1.00

A643336 [912940-89-7]

(R)-2-(1-(tert-Butoxycarbonyl)piperidin-3-yl)acetic acid

Similarity: 1.00

A592532 [1198466-23-7]

2-(3-(tert-Butoxycarbonyl)-3-azabicyclo[3.3.1]nonan-9-yl)acetic acid

Similarity: 1.00

Related Parent Nucleus of
[ 352004-58-1 ]

Piperidines

A312891 [183483-09-2]

1-Boc-Piperidine-3-acetic acid

Similarity: 1.00

A650828 [941289-27-6]

(S)-2-(1-(tert-Butoxycarbonyl)piperidin-3-yl)acetic acid

Similarity: 1.00

A564719 [318536-95-7]

4-(1-(tert-Butoxycarbonyl)piperidin-3-yl)butanoic acid

Similarity: 1.00

A643336 [912940-89-7]

(R)-2-(1-(tert-Butoxycarbonyl)piperidin-3-yl)acetic acid

Similarity: 1.00

A137503 [142247-38-9]

4-(1-(tert-Butoxycarbonyl)piperidin-4-yl)butanoic acid

Similarity: 0.98

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CAS No.: 352004-58-1

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