Prolinol
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424748204
| Name = Prolinol
| ImageFileL1 = D-Prolinol.svg
| ImageClassL1 = skin-invert-image
| ImageFileR1 = L-Prolinol.svg
| ImageClassR1 = skin-invert-image
| IUPACName = (R/S) 2-pyrrolidinemethanol
| OtherNames =
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H52Z235V6Y
| CASNo = 68832-13-3
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Comment = (D-prolinol)
| CASNo1_Ref = {{cascite|changed|??}}
| CASNo1 = 23356-96-9
| CASNo1_Comment = (L-prolinol)
| PubChem = 2724541
| PubChem_Comment = (D-prolinol)
| PubChem1 = 640091
| PubChem1_Comment = (L-prolinol)
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2006673
| ChemSpiderID_Comment = (D-prolinol)
| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 555468
| ChemSpiderID1_Comment = (L-prolinol)
| EC_number1 = 245-605-2
| SMILES = C1C[C@@H](NC1)CO
| SMILES_Comment = (D-prolinol)
| SMILES1 = C1C[C@H](NC1)CO
| SMILES1_Comment = (L-prolinol)
| InChI = 1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m1/s1
| InChI_Comment = (D-prolinol)
| InChIKey = HVVNJUAVDAZWCB-RXMQYKEDSA-N
| InChI1 = 1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m0/s1
| InChI1_Comment = (L-prolinol)
| InChIKey1 = HVVNJUAVDAZWCB-YFKPBYRVSA-N
| RTECS =
}}
|Section2={{Chembox Properties
| C=5 | H=11 | N=1 | O=1
| Appearance = Liquid
| Density = 1.036 g/mL (liquid)
| Solubility =
| MeltingPt =
| BoilingPtC = 74–76
| BoilingPt_notes = at 2 mmHg
| Viscosity =
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards = Irritant
| FlashPtC = 86
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}}
|Section8={{Chembox Related
| OtherCompounds =
}}
}}
Prolinol is a chiral amino-alcohol that is used as a chiral building block in organic synthesis. It exists as two enantiomers: the D and L forms.
Preparation
Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride.{{OrgSynth | last1= Dickman |first1= D. A. |last2= Meyers |first2= A. I. |last3= Smith |first3= G. A. |last4= Gawley |first4= R. E. |prep= CV7P0530 |collvol= 7 |collvolpages= 530 |title= Reduction of α-Amino Acids: L-Valinol |collvolyear= 1990 }}{{OrgSynth |last1= Enders |first1= D. |last2= Fey |first2= P. |last3= Kipphardt |first3= H. |prep= CV8P0026 |collvol= 8 |collvolpages= 26 |title= (S)-(–)-1-Amino-2-Methoxymethylpyrrolidine (SAMP) and (R)-(+)-1-Amino-2-Methoxymethylpyrrolidine (RAMP), Versatile Chiral Auxiliaries |collvolyear= 1993}} Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.
Use
Prolinol is used in broad variety of chemical reactions as chiral ligand, chiral catalyst or chiral auxiliary reagent in the Hajos–Parrish–Eder–Sauer–Wiechert reaction, the Baylis–Hillman reaction, Noyori type reactions and the Michael reaction.
| title = Proline-catalyzed asymmetric reactions
| author = Benjamin List
| journal = Tetrahedron
| year = 2002
| volume = 58
| issue = 28
| pages = 5573–5590
| doi = 10.1016/S0040-4020(02)00516-1
| title = Asymmetric synthesis using chirally modified borohydrides. Part 2. Enantioselective reduction of ketones with polymeric (S)-prolinol–borane reagent
|author1=Shinichi Itsuno |author2=Koichi Ito |author3=Akira Hirao |author4=Seiichi Nakahama | journal = J. Chem. Soc., Perkin Trans. 1
| year = 1984
| volume =
| issue = 12
| pages = 2887–2895
| doi = 10.1039/P19840002887
}}