| Identification | More | [Name]
(S)-3-(Boc-amino)pyrrolidine | [CAS]
122536-76-9 | [Synonyms]
(3S)-(-)-3-(BOC-AMINO)PYRROLIDINE
(3S)-(-)-3-(T-BUTOXYCARBONYLAMINO)PYRROLIDINE
(3S)-(-)-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE
(3S)-()-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE
(3SR)-(+)-(tert-Butoxycarbonylamino)pyrrolidine
BOC-(3S)-(-)-3-AMINOPYRROLIDINE
BOC-(3S)-(-)-(3)APYROLIDI
CARBAMIC ACID, (3S)-3-PYRROLIDINYL-, 1,1-DIMETHYLETHYL ESTER
N-(3S)-(-)-3-(T-BUTOXYCARBONYL)AMINOPYRROLIDINE
PYRROLIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER, (S)
(S)-(-)-3-(BOC-AMINO)PYRROLIDINE
(S)-(+)-3-(BOC-AMINO)PYRROLIDINE
(S)-3-(BOC-AMINO)PYRROLIDINE
(S)-3-N-BOC-AMINO PYRROLIDINE
(S)-3-(TBOC-AMINO)PYRROLIDINE
(S)-3-TERT-BUTOXYCARBONYLAMINOPYRROLIDINE
(S)-PYRROLIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER
(S)-TERT-BUTYL-PYRROLIDINE-3-YLCARBAMATE
TERT-BUTYL (S)-3-PYRROLIDINYLCARBAMATE
TERT-BUTYL (S)-PYRROLIDIN-3-YL CARBAMATE | [EINECS(EC#)]
628-488-6 | [Molecular Formula]
C9H18N2O2 | [MDL Number]
MFCD00143194 | [Molecular Weight]
186.25 | [MOL File]
122536-76-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
50 °C | [Boiling point ]
112°C/0.25mm | [density ]
1.04±0.1 g/cm3(Predicted) | [refractive index ]
-20 ° (C=1, EtOH) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
12.37±0.20(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]/D -21.5±2.0°, c = 1 in ethanol | [Water Solubility ]
Soluble in water. | [Sensitive ]
Air Sensitive | [BRN ]
5377813 | [InChI]
InChI=1S/C9H18N2O2/c1-9(2,3)13-8(12)11-7-4-5-10-6-7/h7,10H,4-6H2,1-3H3,(H,11,12)/t7-/m0/s1 | [InChIKey]
DQQJBEAXSOOCPG-ZETCQYMHSA-N | [SMILES]
C(OC(C)(C)C)(=O)N[C@H]1CCNC1 | [CAS DataBase Reference]
122536-76-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,C | [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 . | [RIDADR ]
3259 | [WGK Germany ]
3
| [F ]
10-23 | [HazardClass ]
8 | [PackingGroup ]
III | [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 crystalline powder | [Uses]
(S)-3-(Boc-amino)pyrrolidine can be used as a building block to prepare:
- 2,4,6-trisubstitued pyrido[3,4-d]pyrimidine derivatives as potent inhibitors against EGFR tyrosine kinase.
- Aminopyrrolidine scaffolds for asymmetric Morita?Baylis-Hillman reaction.
- N-benzyl-3-sulfonamidopyrrolidines as potent bacterial cell division inhibitors.
| [Synthesis]
1. In a 500 mL four-necked flask fitted with a stirrer, thermometer, Dimroth condenser and titration funnel, 17.6 g (0.1 mol, optical purity 99.5% ee) of (S)-3-amino-1-benzylpyrrolidine was added. Subsequently, 158.7 g of water and 0.2 g of cationic DS (produced by Sanyo Chemical Industries, Ltd.) were added and the pH of the mixture was adjusted to 11 ± 0.5 using 48% aqueous sodium hydroxide solution.
2. The mixture was stirred at 50 to 60 °C while 26.2 g (0.12 mol) of di-tert-butyl dicarbonate (DiBoc) was added dropwise for about 2 hours. During the dropwise addition, the pH of the reaction solution was maintained at 11 ± 0.5 using 48% aqueous sodium hydroxide.
3. After completion of the dropwise addition, stirring was continued for 1 hour, after which the reaction solution was cooled to room temperature and the precipitated crystals were separated by filtration.
4. The resulting crystals were dried under vacuum at 50 °C to afford 26.0 g of (S)-1 -benzyl-3-tert-butoxycarbonylaminopyrrolidine in 94.1% yield, 99.1% chemical purity and 99.5% optical purity ee.
5. Using the same apparatus as in Step 1 , 26.0 g (optical purity 99.5% ee) of (S)-1 -benzyl-3-tert-butoxycarbonylaminopyrrolidine, 120 g of water, and 2.6 g of 5% Pd/C (PE-type, 55.27% water content, manufactured by NE Chemcat Corp.) were added. The reaction was stirred at 40°C reaction temperature for 10 hours under hydrogen atmosphere.
6. After confirming the completion of the reaction by GC analysis, the Pd/C was removed by filtration and the filtrate was concentrated to 30 g using an evaporator.
7. The concentrated product was mixed with toluene and concentrated again to 20 g to remove water by azeotropy.
8. 25 g of hexane was slowly added to the concentrated solution with stirring to precipitate crystals, followed by continued stirring in an ice bath for 2 hours.
9. The precipitated crystals were separated by filtration and dried under vacuum to afford 15.4 g of (S)-3-tert-butoxycarbonylaminopyrrolidine in 87.4% yield, 99.5% chemical purity, 99.5% optical purity ee, and 0.4% water content. | [References]
[1] Tetrahedron Asymmetry, 2010, vol. 21, # 11-12, p. 1511 - 1521
[2] Patent: EP1640364, 2006, A1. Location in patent: Page/Page column 10-11 |
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