ChemicalBook--->CAS DataBase List--->84358-13-4

84358-13-4

84358-13-4 Structure

84358-13-4 Structure
IdentificationMore
[Name]

N-BOC-piperidine-4-carboxylic acid
[CAS]

84358-13-4
[Synonyms]

1-(1,1-DIMETHYLETHYL)1,4-PIPERIDINEDICARBOXYLIC ACID
1-BOC-4-PIPERIDINECARBOXYLIC ACID
1-BOC-PIPERIDINE-4-CARBOXYLIC ACID
1-N-BOC-PIPERIDINE-4-CARBOXYLIC ACID
1-(TERT-BUTOXYCARBONYL)PIPERIDINE-4-CARBOXYLIC ACID
AURORA KA-3052
BOC-INP
BOC-INP-OH
BOC-ISONICOT(HEXAHYDRO)-OH
BOC-ISONIPECOTIC ACID
BOC-L-ISONIPECOTIC ACID
BOC-PIC(4)-OH
BOC-PIPERIDINE-4-CARBOXYLIC ACID
BUTTPARK 99\04-45
ISONIPECOTIC ACID, BOC PROTECTED
N-BOC-DL-ISONIPECOTIC ACID
N-BOC-ISONIPECOTIC ACID
N-BOC-PIPERIDINE-4-CARBOXYLIC ACID
N-T-BUTOXYCARBONYL-HEXAHYDROISONICOTINIC ACID
N-T-BUTOXYCARBONYL-PIPERIDINE-4-CARBOXYLIC ACID
[EINECS(EC#)]

700-076-1
[Molecular Formula]

C11H19NO4
[MDL Number]

MFCD00076999
[Molecular Weight]

229.27
[MOL File]

84358-13-4.mol
Chemical PropertiesBack Directory
[Appearance]

White crystalline powder
[Melting point ]

148-153 °C
[Boiling point ]

353.2±35.0 °C(Predicted)
[density ]

1.164±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[form ]

Crystalline Powder
[pka]

4.56±0.20(Predicted)
[color ]

White
[Water Solubility ]

Insoluble in water.
[Detection Methods]

HPLC
[BRN ]

5533442
[Major Application]

peptide synthesis
[InChI]

InChI=1S/C11H19NO4/c1-11(2,3)16-10(15)12-6-4-8(5-7-12)9(13)14/h8H,4-7H2,1-3H3,(H,13,14)
[InChIKey]

JWOHBPPVVDQMKB-UHFFFAOYSA-N
[SMILES]

N1(C(OC(C)(C)C)=O)CCC(C(O)=O)CC1
[CAS DataBase Reference]

84358-13-4(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H335-H315-H319
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
[Hazard Note ]

Irritant
[REACH Registrations]

Active
[HazardClass ]

IRRITANT
[HS Code ]

29333990
[Storage Class]

11 - Combustible Solids
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium carbonate-->1,4-Dioxane-->Di-tert-butyl dicarbonate-->Isonipecotic acid-->N-Boc-Piperidine-4-carboxylic acid methyl ester-->Ethyl N-Boc-piperidine-4-carboxylate-->N,N-Dimethylethylenediamine-->tert-Butanol-->Methanol-->Lithium hydroxide
[Preparation Products]

tert-butyl 4-(1H-benzo[d]iMidazol-2-yl)piperidine-1-carboxylate-->1-Boc-piperidin-4-ylpropionic acid-->1-Boc-4-[methoxy(methyl)carbamoyl]piperidine-->tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate-->N-tert-Butoxycarbonyl-4-(4-toluenesulfonyloxymethyl)piperidine-->1-(Piperidin-4-ylcarbonyl)piperidine-->1-tert-Butoxycarbonylpiperidine-4-carboxylic acidmethyl amide-->4-(5-isopropyl-1,3,4-oxadiazol-2-yl)piperidine
Hazard InformationBack Directory
[Chemical Properties]

White crystalline powder
[Uses]

It is a pharmaceutical intermediate. he camptothecin ester of isonipecotic acid is installed on a triazine dendrimer intermediate obtained through an iterative, scalable route to ultimately yield cationic and PEGylated targets with activities in cell culture comparable to free drug.
[reaction suitability]

reaction type: Boc solid-phase peptide synthesis
[Synthesis]

N-Boc-Piperidine-4-carboxylic acid methyl ester

124443-68-1

N-BOC-piperidine-4-carboxylic acid

84358-13-4

General procedure for the synthesis of 1-Boc-4-piperidinecarboxylic acid from methyl 1-Boc-4-piperidinecarboxylate: 4-tert-butyl-4-methylpiperidine-1,4-dicarboxylate (4.84 g, 20 mmol) and LiOH (2.52 g, 60 mmol) were reacted with 4-tert-butyl-4-methylpiperidine-1,4-dicarboxylate (4.84 g, 20 mmol) and LiOH (2.52 g, 60 mmol) in a mixture of THF (90 mL), MeOH (90 mL) and H2O (30 mL) in a solvent, and the reaction was stirred at room temperature overnight. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was adjusted to pH 2 with aqueous 2N HCl. Subsequently, the reaction mixture was extracted with EtOAc (3 × 20 mL). The organic phases were combined, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (4.6 g, 100.0% yield).

[References]

[1] Patent: WO2012/34526, 2012, A1. Location in patent: Page/Page column 56
[2] Patent: US2013/190307, 2013, A1. Location in patent: Paragraph 0205; 0206
[3] Patent: US2016/102095, 2016, A1. Location in patent: Paragraph 0131
[4] Patent: CN104292233, 2016, B. Location in patent: Paragraph 0047
[5] Patent: WO2016/34134, 2016, A1. Location in patent: Paragraph 00538
Spectrum DetailBack Directory
[Spectrum Detail]

N-BOC-piperidine-4-carboxylic acid(84358-13-4)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

N-BOC-piperidine-4-carboxylic acid, 98%(84358-13-4)
[Alfa Aesar]

N-Boc-isonipecotic acid, 98+%(84358-13-4)
[Sigma Aldrich]

84358-13-4(sigmaaldrich)
[TCI AMERICA]

1-(tert-Butoxycarbonyl)isonipecotic Acid,>96.0%(GC)(T)(84358-13-4)
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