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| | (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE Basic information | | Reactions |
| | (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE Chemical Properties |
| Melting point | 66-72 °C | | alpha | +52° (c=1, CHCl3) | | Boiling point | 406.8±25.0 °C(Predicted) | | density | 1.116±0.06 g/cm3(Predicted) | | refractive index | 55 ° (C=1, CHCl3) | | storage temp. | Sealed in dry,2-8°C | | solubility | sol hexane, benzene, toluene, Et2O, cyclohexane, dichloromethane | | form | Powder | | pka | 13.15±0.29(Predicted) | | color | white to pale-yellow | | Optical Rotation | [α]20/D +55±3°, c = 1% in chloroform stab. with amylenes | | BRN | 4749387 | | InChI | 1S/C18H21NO/c1-19-14-8-13-17(19)18(20,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17,20H,8,13-14H2,1H3/t17-/m0/s1 | | InChIKey | XIJAGFLYYNXCAB-KRWDZBQOSA-N | | SMILES | CN1CCC[C@H]1C(O)(c2ccccc2)c3ccccc3 | | CAS DataBase Reference | 110529-22-1(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | F | 10-34 | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| | (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE Usage And Synthesis |
| Reactions | Catalyst for the enantioselective addition of diethylzinc to α,β-unsaturated aldehydes
| | Chemical Properties | white to slightly yellow crystalline powder | | Uses | (S)-(+)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine is used for chiral ligand for the enantioselective addition of dialkylzincs, alkynylzinc, and cyanomethylzinc bromide to aldehydes; chiral ligand for the enantioselective Reformatsky reaction; chiral ligand for the enantioselective Diels-Alder reaction; chiral auxiliary for asymmetric polymerization.
| | Preparation |
Reaction of Phenylmagnesium Bromide with (S)-N-[(benzyloxy)carbonyl]proline methyl ester and subsequent reduction with Lithium Aluminum Hydride affords the (S)-(+)-2-[Hydroxy(diphenyl)methyl]-1-methylpyrrolidine in 83% overall yield.
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| | (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE Preparation Products And Raw materials |
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