(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE CAS 131878-23-4
(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE Basic information
| Product Name: | (3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE |
| Synonyms: | (R)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE;(R)-(1-BENZYL-PYRROLIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER;(3R)-(+)-1-Benzyl-3-(tert-butoxycarbonylamino)pyrrolidine;tert-butyl N-[(3R)-1-benzylpyrrolidin-3-yl]carbamate;TERT-BUTYL(R)-1-BENZYLPYRROLIDIN-3-YLCARBAMATE;CARBAMIC ACID,[(3R)-1-(PHENYLMETHYL)-3-PYRROLIDINYL]-,1,1-DIMETHYLETHYL ESTER;(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE;(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE 98+% |
| CAS: | 131878-23-4 |
| MF: | C16H24N2O2 |
| MW: | 276.37 |
| EINECS: | |
| Product Categories: | 3-Aminopyrrolidines;Chiral 3-Aminopyrrolidines |
| Mol File: | 131878-23-4.mol |
(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE Chemical Properties
| Melting point | 77-81 °C(lit.) |
| Boiling point | 385.1±31.0 °C(Predicted) |
| density | 1.08 |
| refractive index | 18.5 ° (C=2, EtOH) |
| storage temp. | 2-8°C |
| solubility | almost transparency in Methanol |
| pka | 12.31±0.20(Predicted) |
| form | powder to crystal |
| color | White to Almost white |
| Optical Rotation | [α]20/D +6°, c = 1% in chloroform |
| InChI | 1S/C16H24N2O2/c1-16(2,3)20-15(19)17-14-9-10-18(12-14)11-13-7-5-4-6-8-13/h4-8,14H,9-12H2,1-3H3,(H,17,19)/t14-/m1/s1 |
| InChIKey | PHOIDJGLYWEUEK-CQSZACIVSA-N |
| SMILES | CC(C)(C)OC(=O)N[C@@H]1CCN(C1)Cc2ccccc2 |
| CAS DataBase Reference | 131878-23-4(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Dam. 1 Skin Irrit. 2 STOT SE 3 |
| Synthesis | 24424-99-5 114715-39-8 131878-23-4 The general procedure for the synthesis of (R)-1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine from di-tert-butyl dicarbonate and (R)-1-benzyl-3-amino pyrrolidine was as follows: first, sodium bicarbonate (5.92 g, 70.5 mmol) was dissolved in 118 mL of deionized water, and then this solution was added to a 118 mL acetonitrile solution of (R)-(+)-benzylamino pyrrolidine 1a (5.00 g, 28.4 mmol) in 118 mL of acetonitrile solution. The mixture was stirred at room temperature for 10 minutes. Subsequently, di-tert-butyl dicarbonate (6.22 g, 28.5 mmol) was added and stirring was continued overnight at room temperature. After completion of the reaction, the reaction solution was concentrated under reduced pressure and the residue was extracted three times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by fast column chromatography (eluent ratio methanol: dichloromethane = 2:98). Finally, the solvent was removed in vacuum to afford 4.24 g of tert-butyl (R)-(1-benzylpyrrolidin-3-yl)carbamate in 65.2% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.36-7.26 (m, 5H), 4.86 (bs, 1H), 4.18 (bs, 1H), 3.61 (s, 2H), 2.79 (bs, 1H), 2.65-2.61 (m, 1H), 2.54 (d, J=8.0 Hz, 1H), 2.34- 2.25 (m, 2H), 1.61-1.51 (m, 1H), 1.46 (s, 9H). The specific optical rotation [α]D was +2.5° (c 0.620, CHCl3). |
| References | [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1495 - 1510 [2] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826 [3] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 721 - 739 |
(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE Preparation Products And Raw materials
| Raw materials | Carbamic acid, N-[(1R)-3-[(methylsulfonyl)oxy]-1-[[(methylsulfonyl)oxy]methyl]pr-->(R)-3-(Boc-amino)pyrrolidine-->(R)-DIMETHYL 2-(TERT-BUTOXYCARBONYLAMINO)SUCCINATE-->(S)-1-BENZYL-3-MESYLOXY PYRROLIDINE-->(R)-(+)-2-(Boc-Amino)-1,4-butanediol-->(R)-(-)-1-Benzyl-3-aminopyrrolidine-->Benzaldehyde-->Di-tert-butyl dicarbonate-->(S)-1-Benzyl-3-pyrrolidinol-->Benzylamine |
