| Identification | More | [Name]
(R)-(+)-N-Boc-2-piperidinecarboxylic acid | [CAS]
28697-17-8 | [Synonyms]
1,2-PIPERIDINEDICARBOXYLIC ACID, 1-(1,1-DIMETHYLETHYL) ESTER, (2R)-
(2R)-1-(TERT-BUTOXYCARBONYL)HEXAHYDROPYRIDINE-2-CARBOXYLIC ACID
(2R)-1-(TERT-BUTOXYCARBONYL)PIPERIDINE-2-CARBOXYLIC ACID
2(R)-1-(TERT-BUTOXYCARBONYL)PIPERIDINECARBOXYLIC ACID
BOC-D-HOMOPROLINE
BOC-D-HOMOPRO-OH
BOC-D-HOPRO-OH
BOC-D-PIC(2)-OH
BOC-D-(+)-PIPECOLIC ACID
BOC-D-PIPECOLIC ACID
BOC-D-PIPECOLINIC ACID
BOC-D-PIPERIDINE-2-CARBOXYLIC ACID
BOC-D-PIP-OH
BOC-(R)-(+)-PIPERIDINE-2-CARBOXYLIC ACID
BOC-R-PIP-OH
(D)-N-BOC-PIPECOLIC ACID
(D)-N-(T-BUTOXYCARBONYL)PIPECOLIC ACID
(D)-N-(TERT-BUTOXYCARBONYL)PIPECOLIC ACID
N-ALPHA-T-BOC-D-PIPECOLIC ACID
N-ALPHA-T-BUTOXYCARBONYL-D-HOMOPROLINE | [EINECS(EC#)]
200-533-0 | [Molecular Formula]
C11H19NO4 | [MDL Number]
MFCD00237380 | [Molecular Weight]
229.27 | [MOL File]
28697-17-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
116-119 °C(lit.)
| [alpha ]
68 º (c=1 in acetic acid) | [Boiling point ]
353.2±35.0 °C(Predicted) | [density ]
1.164±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT. | [solubility ]
Soluble in 2ml dimethyl formamide 0.3gram. | [form ]
Crystalline Powder | [pka]
4.03±0.20(Predicted) | [color ]
White to brown | [Optical Rotation]
[α]23/D 63.5±3°, c = 1 in acetic acid | [BRN ]
480023 | [Major Application]
peptide synthesis | [InChI]
1S/C11H19NO4/c1-11(2,3)16-10(15)12-7-5-4-6-8(12)9(13)14/h8H,4-7H2,1-3H3,(H,13,14)/t8-/m1/s1 | [InChIKey]
JQAOHGMPAAWWQO-MRVPVSSYSA-N | [SMILES]
CC(C)(C)OC(=O)N1CCCC[C@@H]1C(O)=O | [CAS DataBase Reference]
28697-17-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [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 .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
It is also applied as catalytic agent and petrochemical additive. It is also an important organic intermediate used in agrochemicals, pharmaceuticals and dyestuff fields. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of (R)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid from di-tert-butyl dicarbonate and D-(+)-2-piperidinic acid was as follows: to a 1000 mL round-bottomed flask were added D-(+)-2-piperidinic acid (8.0 g, 0.062 mol), di-tert-butyl dicarbonate (14.8 g, 0.068 mol), sodium bicarbonate (26.04 g, 0.310 mol) and methanol (400 mL). The mixture was stirred and reacted at room temperature for 24 hours. Upon completion of the reaction, methanol was removed by distillation under reduced pressure. The residue was dissolved in water and subsequently washed three times with ether. The pH of the aqueous phase was adjusted to 2 with saturated potassium bisulfate solution and then extracted three times with dichloromethane. The organic phases were combined, washed three times with saturated saline, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography with the eluent being a mixed solvent of petroleum ether/ethyl acetate/acetic acid, resulting in 12.48 g of white solid product in 87.8% yield. The product was characterized by 1H-NMR (400 MHz, DMSO) and EI-MS: 1H-NMR δ 12.71 (1H, s), 4.61 (1H, d, J = 28.8 Hz), 3.82 (1H, d, J = 12 Hz), 2.93 (1H, m), 2.06 (1H, s), 1.62 (3H, m), 1.39 (11H, m); EI-MS m/z: 229.1 [M]+. | [References]
[1] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 591 - 601
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 9, p. 1550 - 1557
[3] ChemMedChem, 2013, vol. 8, # 4, p. 577 - 581
[4] Patent: EP2805947, 2014, A1. Location in patent: Paragraph 0074-0075
[5] Patent: US2015/126500, 2015, A1. Location in patent: Paragraph 0127; 0128 |
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