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Quality Control of 4-Amino-1-Boc-piperidine-4-carboxylic acid Purity: 97% SDS Specification

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NMR

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Product Details of 4-Amino-1-Boc-piperidine-4-carboxylic acid

CAS No. :	183673-71-4
Formula :	C₁₁H₂₀N₂O₄
M.W :	244.29
SMILES Code :	O=C(C1(N)CCN(C(OC(C)(C)C)=O)CC1)O
Synonyms :	1-Boc-4-Aminopiperidine-4-carboxylic acid
MDL No. :	MFCD01318728
InChI Key :	YNHLVALLAURVJF-UHFFFAOYSA-N
Pubchem ID :	693797

Safety of 4-Amino-1-Boc-piperidine-4-carboxylic acid

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of 4-Amino-1-Boc-piperidine-4-carboxylic acid

* 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 [ 183673-71-4 ]

[ 183673-71-4 ] Synthesis Path-Downstream 1~35

1
[ 102774-86-7 ]
[ 183673-71-4 ]
[ 183673-66-7 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7650 - 7651.

2
[ 183673-68-9 ]
[ 183673-71-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2448 - 2451.
[2]Organic Syntheses,2005,vol. 81,p. 213 - 224.
[3]Journal of Organic Chemistry,1996,vol. 61,p. 7650 - 7651.
[4]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2519 - 2522.

3
[ 183673-71-4 ]
[ 2937-50-0 ]
[ 495414-58-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2519 - 2522.

4
[ 67-56-1 ]
[ 183673-71-4 ]
[ 590-86-3 ]
[ 630132-95-5 ]

References: [1]Organic Letters,2005,vol. 7,p. 5521 - 5524.

5
[ 188440-21-3 ]
[ 183673-71-4 ]
[ 1026484-91-2 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 550 - 565.

6
[ 183673-71-4 ]
[ 18908-07-1 ]
4-[3-(3-methoxy-phenyl)-ureido]-piperidine-1,4-dicarboxylic acid mono-<i>tert</i>-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2171 - 2178.

7
[ 501-53-1 ]
[ 183673-71-4 ]
[ 288154-16-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2448 - 2451.

8
[ 24424-99-5 ]
[ 183673-71-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2448 - 2451.
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2519 - 2522.
[3]Journal of Organic Chemistry,1996,vol. 61,p. 7650 - 7651.

9
[ 41979-39-9 ]
[ 183673-71-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2448 - 2451.

10
[ 13625-39-3 ]
[ 183673-71-4 ]

11
[ 183673-71-4 ]
C₃₂H₃₄N₄O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2448 - 2451.

12
[ 183673-71-4 ]
[ 940290-02-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2448 - 2451.

13
[ 183673-71-4 ]
[ 940290-03-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2448 - 2451.

14
[ 183673-71-4 ]
[ 940290-04-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2448 - 2451.

15
[ 183673-71-4 ]
[ 937806-34-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2171 - 2178.

16
[ 183673-71-4 ]
4'-[3-(3-methoxy-phenyl)-2,4-dioxo-1,3,8-triaza-spiro[4.5]dec-8-ylmethyl]-biphenyl-3-carbonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2171 - 2178.

17
[ 183673-71-4 ]
[ 630131-43-0 ]

References: [1]Organic Letters,2005,vol. 7,p. 5521 - 5524.

18
[ 73390-11-1 ]
[ 183673-71-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2519 - 2522.

19
[ 183673-71-4 ]
3-(3,5-bis-trifluoromethyl-phenyl)-8-(naphthalene-1-carbonyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2519 - 2522.

20
[ 183673-71-4 ]
3-(3,5-bis-trifluoromethyl-benzyl)-2,4-dioxo-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid <i>m</i>-tolylamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2519 - 2522.

21
[ 183673-71-4 ]
3-(3,5-bis-trifluoromethyl-phenyl)-8-(2,4,6-trimethyl-benzoyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2519 - 2522.

22
[ 183673-71-4 ]
3-biphenyl-3-ylmethyl-8-(3,5-bis-trifluoromethyl-benzoyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2519 - 2522.

23
[ 183673-71-4 ]
3-(3,5-bis-trifluoromethyl-benzyl)-8-(2-naphthalen-1-yl-ethanesulfonyl)-1,3,8-triaza-spiro[4.5]decane-2,4-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2519 - 2522.

24
[ 79099-07-3 ]
[ 183673-71-4 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7650 - 7651.

25
[ 40064-34-4 ]
[ 183673-71-4 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7650 - 7651.
[2]Journal of Organic Chemistry,1996,vol. 61,p. 7650 - 7651.

26
[ 183673-70-3 ]
[ 183673-71-4 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 7650 - 7651.

27
[ 183673-71-4 ]
[ 590-86-3 ]
[ 630132-94-4 ]

Yield	Reaction Conditions	Operation in experiment
83%		A slurry of 1-tert-butyl 4-amino-piperidine-1, 4-dicarboxylate (0.489 g, 2.00 mmol) in anhydrous methanol (10.0 mL) was treated with isovaleraldehyde (0.215 mL, 2.00 mmol). After stirring 3 h at ambient temperature, sodium cyanoborohydride (0.088 g, 1.40 mmol) was added. After stirring 3 d at ambient temperature, the title compound was collected by filtration as a white solid (0.523 g, 83percent). MS (ES+) [M/E] 315 [M+H] +.

References: [1]Patent: WO2003/99801,2003,A1 .Location in patent: Page 47.

28
[ 186581-53-3 ]
[ 183673-71-4 ]
[ 321997-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane; at 20℃; for 0.5h;	Intermediate 65: Methyl 1-BOC-4-amino-4-piperidinecarboxylate To a solution of l-BOC-4-amino-4-piperidinecarboxylic acid (2.00 g, 8.2 mol) in MeOH (300 mL) and DCM (300 mL) was added diazomethane slowly until the reaction solution became to pale yellow. The reaction mixture was stirred at room temperature for additional 30 min. and concentrated in vacuo to give the title compound. MS [M+H] = 393 (M+1)

References: [1]Patent: WO2005/47253,2005,A1 .Location in patent: Page/Page column 49.

29
[ 183673-71-4 ]
[ 18107-18-1 ]
[ 321997-89-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-ethyl-N,N-diisopropylamine; In methanol; hexane; acetonitrile;	(a) Methyl 4-amino-1-tert-butoxycarbonylpiperidine-4-carboxylate 4-Amino-1-tert-butoxycarbonylpiperidine-4-carboxylate (5g) in acetonitrile (22ml) and methanol (2ml) was treated with di-isopropylethylamine (3.65ml) and trimethylsilyldiazomethane (2M in hexane, 13.9ml). After overnight stirring and evaporation of solvent, the crude product was chromatographed on silica gel (0-50% ethyl acetate/petrol) to give a yellow oil (4g, 76%). MS (+ve ion electrospray) m/z 259 (MH+).

References: [1]Patent: EP1214314,2005,B1 .Location in patent: Page/Page column 17.

30
[ 541-41-3 ]
[ 183673-71-4 ]
[ 392331-43-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	With pyridine; sodium hydroxide; In ethanol; dichloromethane;	92b) 1-(tert-Butoxycarbonyl)-4-(ethoxycarbonylamino)-4-piperidinecarboxylic Acid Ethyl chlorocarbonate (0.95 ml) was added dropwise to a solution of <strong>[183673-71-4]4-amino-1-(tert-butoxycarbonyl)-4-piperidinecarboxylic acid</strong> (0.98 g) obtained in Example 92a) and pyridine (0.8 g) in methylene chloride (50 ml) at -30° C., and the mixture was stirred further at room temperature for 5 hours. The reaction mixture was concentrated, the residue was diluted with water, adjusted to pH 3 with an aqueous potassium hydrogensulfate, and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column to obtain colorless oil (0.9 g). A 1 N aqueous sodium hydroxide solution (6 ml) was added to a solution of the resulting oil in ethanol (5 ml), the mixture was stirred at room temperature for 18 hours, and the reaction mixture was concentrated under reduced pressure. The residue was diluted with water, the mixture was adjusted to pH 3 with an aqueous potassium hydrogensulfate solution, and extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain the title compound (0.61 g, 48percent). NMR (CDCl3) delta: 1.25 (3H, t, J=7.1), 1.46 (9H, s), 1.90-2.20 (4H, m), 3.00-3.22 (2H, m), 3.76-3.98 (2H, m), 4.13 (2H, q, J=7.1), 5.11 (1H, bs), 7.47 (1H, bs). IR (KBr): 1698, 1674, 1534, 1433 cm-1.

References: [1]Patent: US2003/187023,2003,A1 .

31
[ 98-74-8 ]
[ 183673-71-4 ]
[ 18107-18-1 ]
[ 321997-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; hexane;	a) 4-Amino-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester. To a slurry of 4-amino-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (13.9 g) in methanol (150 mL) and tetrahydrofuran (100 mL) cooled to 0 C. is added dropwise over 4 hours 2 M trimethylsilyldiazomethane in hexane (57 mL) followed by 4-nitrophenylsulfonyl chloride (2.0 g). The solvents are evaporated under vacuum and the crude product is used in the next step without further purification.

References: [1]Patent: US2003/139414,2003,A1 .

Yield	Reaction Conditions	Operation in experiment
		Step 4 Synthesis of 1-Boc-4-aminopiperidine-4-carboxylic acid (8) In a 2L Erlenmeyer flask equipped with a stirring bar, 1-Boc-4-piperidinespiro-5'-(di-t-Boc)-hydantoin (5) (4.23 g, 9.0 mmol) was suspended in THF (800 mL). To this suspension was added 1N LiOH (72 mL, 72 mmol) with vigorous stirring. The resulting white suspension was stirred for 24 hrs. The final reaction mixture was concentrated with reduced pressure, extracted with Et2O (2*125 mL), and the pH adjusted to 7 with a solution of 20percent citric acid. The resulting solid was filtered and dried in vacuo to yield 1-Boc-4-aminopiperidine-4-carboxylic acid 8 (1.54 g, 70percent). 1H NMR (250 MHZ, C5D5N) d 4.45 (br, 1H), 4.23 (br, 1H), 3.71(br, 2H), 2.87 (dt, 2H), 2.35 (br, 1H), 1.86 (br d, 2H), 1.55, 1.54 (2s, 9H).

33
[ 183673-71-4 ]
[ 286459-94-7 ]
[ 287408-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; triethylamine; In 1,4-dioxane; water; ethyl acetate;	Step 1 4-Amino-1-(tert-butoxycarbonyl)-4-piperidinecarboxylic acid (1.0 g, 4.09 mmol) in dioxane (5 mL) and water (2.5 mL) was treated with triethylamine (0.63 mL, 4.5 mmol) and 0.8 mL of 5 N aqueous sodium hydroxide and 4-(2-butynyloxy)phenyl sulfonyl chloride (1.0 g, 4.09 mmol) was then added. After 40h, ethyl acetate and 1N aqueous hydrochloric acid was added. The organic phase was washed an additional 2* with 1N aqueous hydrochloric acid and once with brine, then dried over anhydrous magnesium sulfate to give an oil (0.98 g) which was chromatographed on silica gel eluding with dichloromethane/methanol to give 1-(tert-butoxycarbonyl)4-([4-(2-butynyloxy)phenyl]sulfonyl} amino)-4-piperidinecarboxylic acid as a white powder (0.36 g). Electrospray Mass Spec 453.1(+H)+.

References: [1]Patent: US6225311,2001,B1 .

34
[ 13139-17-8 ]
[ 183673-71-4 ]
[ 288154-16-5 ]

Yield	Reaction Conditions	Operation in experiment
	With aq. sodium hydroxide; In 1,2-dimethoxyethane; aqueous sodium hydroxide;	(a) Allyl 4-benzyloxycarbonylaminopiperidine-4-carboxylate. 4-Amino-1-tert-butoxycarbonylpiperidine-4-carboxylic acid (18.0 g) was dissolved in 0.03M aqueous sodium hydroxide (750 mL), and 1,2-dimethoxyethane (100 mL). The pH was adjusted to 9.5 with dilute hydrochloric acid, and the suspension was added to an ice-cold solution of N-(benzyloxycarbonyloxy)succinimide (28.8 g) in 1,2-dimethoxyethane (100 mL). The pH was kept at 9.5 by addition of aq. sodium hydroxide, and the mixture was stirred at room temperature. More N-(benzyloxycarbonyloxy)succinimide (3 g) was added after 7 h, then stirring continued overnight. After evaporation to remove the 1,2-dimethoxyethane, the aqueus residue was extracted with ether then acidified to pH 4 and extracted with ethyl acetate. This extract was washed with dilute hydrochloric acid, water and brine, dried and evaporated. Trituration of the oily residue gave 4-benzyloxycarbonylamino-1-tert-butoxycarbonylpiperidine-4-carboxylic acid (23 g).
	In sodium hydroxide; 1,2-dimethoxyethane;	(a) Methyl 4-benzyloxycarbonylamino-1-tert-butoxycarbonylpiperidine-4-carboxylate. 4-Amino-1-tert-butoxycarbonylpiperidine-4-carboxylic acid (18.0 g) was dissolved in 0.03M aqueous sodium hydroxide (750 ml), and 1,2-dimethoxyethanol (DME, 100 ml). The pH was adjusted to 9.5 with dilute hydrochloric acid, and the suspension was added to an ice-cold solution of N-(benzyloxycarbonyloxy)succinimide (28.8 g) in DME (100 ml). The pH was kept at 9.5 by addition of aqueous sodium hydroxide, and the mixture was stirred at room temperature. More N-(benzyloxycarbonyloxy)succinimide (3 g) was added after 7 hours, then stirring was continued overnight. After evaporation, the aqueous residue was extracted with ether then acidified to pH4 and extracted with ethyl acetate. This extract was washed with dilute hydrochloric acid, water and brine, dried and evaporated. Trituration of the oily residue gave 4-benzyloxycarbonylamino-1-tert-butoxycarbonylpiperidine-4-carboxylic acid (23 g).

References: [1]Patent: US2004/38998,2004,A1 .
[2]Patent: US2004/53928,2004,A1 .

35
C₁₆H₁₈ClNO₄S₂ [ No CAS ]
[ 183673-71-4 ]
[ 286459-94-7 ]
[ 287408-73-5 ]

Yield	Reaction Conditions	Operation in experiment
		4-Amino-1-(tert-butoxycarbonyl)-4-piperidinecarboxylic acid (1.0 g, 4.09 mmol) in dioxane (5 mL) and water (2.5 mL) was treated with triethylamine (0.63 mL, 4.5 mmol) and 0.8 mL of 5N aqueous sodium hydroxide and 4-(2-butynyloxy)phenyl sulfonyl chloride (1.0 g, 4.09 mmol) was then added. After 40h, ethyl acetate and 1N aqueous hydrochloric acid was added The organic phase was washed an additional 2X with 1N aqueous hydrochloric acid and once with brine, then dried over anhydrous magnesium sulfate to give an oil (0.98 g) which was chromatographed on silica gel eluting with dichloromethane/methanol to give 1-(tert-butoxycarbonyl)-4-([4-(2-butynyloxy)phenyl]sulfonyl} amino)-4-piperidinecarboxylic acid as a white powder (0.36 g). Electrospray Mass Spec 453.1 (M+H)+.

References: [1]Patent: EP1144368,2004,B1 .Location in patent: Page 116.

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• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

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Code	Phrase
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Code	Phrase
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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 183673-71-4

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CAS No.: 183673-71-4

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[ 183673-71-4 ] Synthesis Path-Downstream 1~35

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