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• W1912384174 abstract "(S)[112068-01-6] C17H19NO (MW 253.37)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/s1InChIKey = OGCGXUGBDJGFFY-INIZCTEOSA-N(R)[22348-32-9]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-/m1/s1InChIKey = OGCGXUGBDJGFFY-MRXNPFEDSA-N((S) ·HCl)[16226-54-3] C17H20ClNO (MW 289.83)InChI = 1S/C17H19NO.ClH/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;1H/t16-;/m0./s1InChIKey = XYSYRXOJSOXZPT-NTISSMGPSA-N(precursor to several chiral oxazaborolidine catalysts1 used for the enantioselective reduction of prochiral ketones2, 3)Alternate Name: diphenylprolinol.Physical Data: mp 79–79.5 °C (hexane); 80–82 °C (EtOH). [α]589 −54.3° (c 0.261, MeOH); −68.1° (c 3.17, CHCl3) for the (S)-enantiomer.Solubility: very sol THF, CH2Cl2, MeOH, toluene.Preparative Methods: addition of Phenylmagnesium Bromide to (S)-proline-N-carboxyanhydride (73% overall from proline).4 Addition of N-benzyl-(S)-proline ethyl ester to phenylmagnesium chloride followed by catalytic hydrogenolysis (49% overall from proline).5 Addition of N-(benzyloxycarbonyl)-(S)-proline methyl ester to phenylmagnesium chloride (50% overall yield from proline).3a,c Addition of phenylmagnesium bromide to N-(ethyloxycarbonyl)-(S)-proline methyl ester followed by alkaline hydrolysis (65% overall yield from proline).6 Addition of (S)-proline ethyl ester hydrochloride to phenylmagnesium chloride (20–26% overall yield from proline, ca. 80% ee).7 Enantioselective deprotonation of N-Boc-pyrrolidine with sec-Butyllithium/(−)-Sparteine followed by reaction with benzophenone to give (R)-diphenylprolinol (63% yield from pyrrolidine).8 Addition of phenylmagnesium chloride to methyl pyroglutamate followed by reduction with borane to give racemic diphenylprolinol (51% yield) which can be resolved as its O-acetylmandelate salt to give the (R)- and (S)-enantiomers (30% yield from the racemate).3b Addition of lithiated N-nitrosopyrrolidine to benzophenone to give racemic diphenylprolinol (58–60% yield based on benzophenone).9Purification: recrystallization from hexane, ethanol, or methanol/water.Handling, Storage, and Precautions: no special information available. In general, however, it is advisable that all reactions with this reagent be conducted in a well ventilated fume hood. Care should be exercised to avoid contact of this reagent and the derived oxazaborolidine catalyst with the eyes and skin." @default.
• W1912384174 created "2016-06-24" @default.
• W1912384174 creator A5007341936 @default.
• W1912384174 creator A5008283426 @default.
• W1912384174 creator A5034044651 @default.
• W1912384174 creator A5046597133 @default.
• W1912384174 date "2012-09-14" @default.
• W1912384174 modified "2023-09-28" @default.
• W1912384174 title "α,α-Diphenyl-2-pyrrolidinemethanol" @default.
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• W1912384174 doi "https://doi.org/10.1002/047084289x.rd435m.pub2" @default.
• W1912384174 hasPublicationYear "2012" @default.
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