| Identification | More | [Name]
L-1-Boc-Nipecotic acid | [CAS]
88495-54-9 | [Synonyms]
1-(BOC)-3-PIPERIDINE-CARBOXYLIC ACID
1-BOC-PIPERIDINE-3-CARBOXYLIC ACID
1-N-BOC-PIPERIDINE-3-CARBOXYLIC ACID
1-(TERT-BUTOXYCARBONYL)-3-PIPERIDINECARBOXYLIC ACID
1-(TERT-BUTOXYCARBONYL)PIPERIDINE-3-CARBOXYLIC ACID
BOC-3-CARBOXYPIPERIDINE
BOC-DL-NIPC-OH
BOC-DL-NIPECOTIC ACID
BOC-DL-NIP-OH
BOC-DL-PIC(3)-OH
BOC-L-NIP-OH
BOC-NIP
BOC-NIP-OH
BOC-(R,S)-NIPECOTIC ACID
BOC-(R,S)-NIP-OH
BOC-(S)-NIPECOTIC ACID
BOC-(S)-NIP-OH
BOC-(S)-PIPERIDINE-3-CARBOXYLIC ACID
L-1-BOC-NIPECOTIC ACID
N-ALPHA-T-BOC-3-CARBOXYPIPERIDINE | [Molecular Formula]
C11H19NO4 | [MDL Number]
MFCD00673775 | [Molecular Weight]
229.27 | [MOL File]
88495-54-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
159-162 °C(lit.)
| [Boiling point ]
353.2±35.0 °C(Predicted) | [density ]
1.164±0.06 g/cm3(Predicted) | [storage temp. ]
Store at 0-5°C | [form ]
solid | [pka]
4.49±0.20(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]22/D +57°, c = 1 in chloroform | [InChI]
InChI=1S/C11H19NO4/c1-11(2,3)16-10(15)12-6-4-5-8(7-12)9(13)14/h8H,4-7H2,1-3H3,(H,13,14)/t8-/m0/s1 | [InChIKey]
NXILIHONWRXHFA-QMMMGPOBSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CCC[C@H](C(O)=O)C1 | [CAS DataBase Reference]
88495-54-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,N | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R50:Very Toxic to aquatic organisms. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3077 9/PG 3 | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
1-Boc-L-nipecotic acid is used as an organic chemical synthesis intermediate. | [Synthesis]
The general procedure for the synthesis of 1-BOC-piperidine-3-carboxylic acid from di-tert-butyl dicarbonate and 3-piperidinecarboxylic acid was as follows:
1. To a solution of piperidine-3-carboxylic acid (50.0 g, 387.5 mmol) in tert-butanol (464.0 mL) was slowly added 1N NaOH solution (464.0 mL) at 0 °C and stirred for 10 min.
2. Di-tert-butyl dicarbonate (Boc-anhydride, 143.6 g, 659.0 mmol) was then added.
3. The reaction mixture was stirred continuously at room temperature for 12 hours.
4. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and then neutralized to neutrality with 1N HCl solution.
5. The precipitated solid product was collected by filtration and dried to give 1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (1, 86.0 g, 97% yield) as a white solid.
Product characterization data: 1H NMR (400 MHz, DMSO-d6) δ 1.38 (s, 9H), 1.47 (m, 1H), 1.59 (dt, J = 3.8 Hz, 1H), 1.87 (m, 1H), 2.28 (m, 1H), 2.77-2.84 (dt, J = 2.5,3.0 Hz, 1H), 3.0 (brs. 1H), 3.67 (d, J = 11.0 Hz, 1H), 3.87 (brs, 1H), 12.2 (s, 1H). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2118 - 2122
[2] Patent: WO2014/149164, 2014, A1. Location in patent: Paragraph 00604
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 7, p. 1719 - 1728
[4] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 966 - 973
[5] European Journal of Organic Chemistry, 2005, # 4, p. 673 - 682 |
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