diphenyl(2S)-pyrrolidin-2-ylmethanol

• ChemBase ID: 69333
• Molecular Formular: C17H19NO
• Molecular Mass: 253.33886
• Monoisotopic Mass: 253.14666423
• SMILES: N1[C@@H](CCC1)C(O)(c1ccccc1)c1ccccc1
• Canonical SMILES: OC(c1ccccc1)(c1ccccc1)[C@@H]1CCCN1
• InChI: InChI=1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2/t16-/m0/s1
• InChIKey: OGCGXUGBDJGFFY-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenyl(2S)-pyrrolidin-2-ylmethanol
• IUPAC Traditional name: diphenyl(2S)-pyrrolidin-2-ylmethanol
• Synonyms: (S)-(-)-2-(Diphenylhydroxymethyl)pyrrolidine; α,α-Diphenyl-L-prolinol; (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol; (S)-α,α-Diphenyl-2-pyrrolidinemethanol; (S)-2-(Diphenylhydroxymethyl)pyrrolidine; α,α-Diphenyl-L-prolinol; Diphenyl[(2R)-(+)-pyrrolidin-2-yl]methanol; (R)-(+)-alpha,alpha-Diphenylprolinol; (2R)-(+)-2-[Hydroxy(diphenyl)methyl]pyrrolidine; (S)-Diphenyl(pyrrolidin-2-yl)methanol; (S)-(-)-Alpha,alpha-Diphenyl-2-pyrrolidinemethanol; (S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol; (S)-(-)-alpha,alpha-Diphenylprolinol; (S)-(-)-2-(二苯基羟甲基)吡咯烷; α,α-二苯基-L-脯氨醇; (S)-(-)-α,α-二苯基脯氨醇; (S)-α,α-二苯基-2-吡咯烷甲醇; (S)-2-(二苯基羟甲基)吡咯烷; (S)-(+)-α,α-二苯基脯氨醇

Database IDs

• CAS Number: 22348-32-9; 112068-01-6
• MDL Number: MFCD00075506
• Beilstein Number: 17103; 6060893
• PubChem SID: 24862899; 162035060; 24879275
• PubChem CID: 2724899

CALCULATED PROPERTIES

• Acid pKa: 12.901563
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.35732114
• LogD (pH = 7.4): 0.039381664
• Log P: 2.8763463
• Molar Refractivity: 77.1829 cm^3
• Polarizability: 30.58561 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 76-78°C; 77°C; 77-80 °C; 77-80 °C(lit.)
• Optical Rotation: [α]20/D -67°, c = 3 in chloroform; [α]20/D -69±2°, c = 3% in chloroform; -57.5 (c=3 in methanol)

Safety Information

• Storage Warning: IRRITANT; Irritant/Store under Nitrogen
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37; 26-37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 95+%; 98%; 99%
• Grade: purum
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C17H19NO

DETAILS

Sigma Aldrich - 368199

Packaging
1, 5 g in glass bottle
Application
Used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.1

Sigma Aldrich - 552526

Legal Information
A Product of Onyx Scientific, U.K.

Sigma Aldrich - 43182

Other Notes
The cyclic borane adduct, an oxazaborolidine, is an efficient catalyst for enantioselective reductions of ketones with borane (CBS-reduction)1,2,3,4

REFERENCES

• For use in conjunction with borane generated in situ using NaBH₄ and iodine, see: Tetrahedron, 50, 6411 (1994). For an optimized in situ procedure for generation and use of the oxazaborolidine from BMS, see: Tetrahedron: Asymmetry, 7, 3147 (1996). In a comparison with other oxazaborolidine precursors, diphenylprolinol gave the best results (same ref.). For in situ generation of an asymmetric reduction system using trimethyl borate and BMS, see: Synlett, 273 (1997). For the generation and use of the phenyl oxazaborolidine, using Benzeneboronic acid, A14257, see: Tetrahedron Lett., 31, 7415 (1990); 32, 7175 (1991); J. Org. Chem., 57, 7115 (1992). For a detailed comparative study of various alkyl- and aryl-substituted borolidines, see: J. Org. Chem., 56, 763 (1991). For a process for the in situ formation of butyl oxazaborolidines using 1-Butylboronic acid, A13725, see: Tetrahedron Lett., 33, 4141 (1992). For use for the catalytic enantioselective synthesis of chiral monosubstituted oxiranes, see: Tetrahedron Lett., 34, 5227 (1993).
• For reviews of oxazaborolidines as enantioselective catalysts, see: Angew. Chem. Int. Ed., 31, 729 (1992); 37, 1986 (1998); Tetrahedron: Asymmetry, 3, 1475 (1992). For reviews of the asymmetric reduction of ketones, see: Synthesis, 605 (1992); Chem. Ind. (London), 552 (1994).
• See also the preformed catalyst (S)-2-Methyl-CBS-oxazaborolidine, L14583, and (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.
• Precursor of Corey, Bakshi and Shibata's oxazaborolidine derivatives (CBS catalysts) for enantioselective reduction of prochiral ketones: J. Am. Chem. Soc., 109, 5551 (1987). Ketones are not reduced rapidly by either borane-THF or the oxazaborolidine alone but together they form a complex which reduces ketones rapidly and stereoselectively, permitting reduction with very high ee in the presence of a catalytic amount of the oxazaborolidine: J. Am. Chem. Soc., 109, 7925 (1987).