103621-10-9

Basic information

• Product Name: N-[(R)-2'-hydroxy-1'-phenylethyl]-(S)-1-phenyl-1-ethylamine
• Synonyms: N-[(R)-2'-hydroxy-1'-phenylethyl]-(S)-1-phenyl-1-ethylamine
• CAS NO: 103621-10-9
• Molecular Weight: 241.333
• Mol File: 103621-10-9.mol

Chemical Properties

• CAS DataBase Reference: N-[(R)-2'-hydroxy-1'-phenylethyl]-(S)-1-phenyl-1-ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(R)-2'-hydroxy-1'-phenylethyl]-(S)-1-phenyl-1-ethylamine(103621-10-9)
• EPA Substance Registry System: N-[(R)-2'-hydroxy-1'-phenylethyl]-(S)-1-phenyl-1-ethylamine(103621-10-9)

Safety Data

• Hazardous Substances Data: 103621-10-9(Hazardous Substances Data)

Upstream product

• 126927-36-4 methyl N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-(1-phenylethyl)amino carbonate 
• 2935-35-5 (S)-2-phenylglycine 
• 20989-17-7 (2S)-2-phenylglycinol 
• 126927-05-7 N-ethylidene-2-(phenylmethoxy)-1-phenylethanamine N-oxide 
• 127001-22-3 (+/-)-phenylglycinol benzyl ether 
• 127001-22-3 (S)-1-phenyl-2-(phenylmethoxy)ethylamine 
• 127001-24-5 (+/-)-N-hydroxy-2-(phenylmethoxy)-1-phenylethanamine 
• 126927-02-4 (+)-(S)-N-hydroxy-2-(phenylmethoxy)-1-phenylethanamine 
• 126927-07-9 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-1-phenylethanamine 
• 127001-25-6 (-)-(S)-N-benzylidene-2-(phenylmethoxy)-1-phenylethanamine N-oxide 
• 127001-23-4 (+/-)-2-(phenylmethoxy)-N-<(2-chlorobenzoyl)oxy>-1-phenylethanamine 
• 127001-23-4 (+)-(S)-2-(phenylmethoxy)-N-<(2-chlorobenzoyl)oxy>-1-phenylethanamine 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 126927-40-0 (1'R*,1R*)-N-(2'-methoxy-1'-phenylethyl)-N-methyl-1-phenylethanamine 
• 90933-77-0 N-(2'-methoxy-1'-phenylethyl)-1-phenylethanamine 
• 90933-77-0 <2-Methoxy-(R)-1-phenylethyl><(S)-1-phenylethyl>amine 

Relevant articles and documents

Diastereoselective addition of organolithiums to 1,3-oxazolidines complexed with aluminum tris(2,6-diphenylphenoxide) (ATPH)

1,3-Oxazolidines were easily obtained by condensation of N-substituted (R)-phenylglycinol with aldehydes. Addition of organolithium reagents to 1,3-oxazolidines by complexation with the bulky Lewis acid aluminum tris(2,6-diphenylphenoxide) (ATPH) readily produced the corresponding chiral amines with good yield and high diastereoselectivity. The configuration of the new stereogenic center was shown to be opposite to that of adducts obtained for the same 1,3-oxazolidines using Grignard reagents. The best diastereoselectivity was achieved using N-isopropyl-1,3-oxazolidines. The mechanism of addition was deduced by determining the stereochemistry of the iminium-aluminum complex by NOE experiments.

Asymmetric synthesis of two new conformationally constrained lysine derivatives

The asymmetric synthesis of the conformationally constrained L- and D-lysine derivatives methyl (1S,8S)-1-amino-8-tert-butoxycarbonylamino-1,2,3,4,5,6,7, 8-octahydroanthracene-1-carboxylate (4) and methyl (1R,8S)-1-amino-8-tert-butoxycarbonylamino-1,2,3,4,5,6,7, 8-octahydroanthracene-1-carboxylate (5), respectively are described. Application of the Bucherer hydantoin synthesis to the carbonyl group of 2′,3′,4′,5′,6′,7′-hexahydrospiro[1, 3-ethylenedithiole-2,1′-anthracen]-8′-one (18), which was prepared from 1,8-dichloroanthraquinone (14) in nine steps and the deprotection of the masked second ketone of 18 yields rac-21. The latter is the precursor for a novel asymmetric reductive amination protocol using (R)-phenylglycinol as a chiral amino auxiliary and NaBH(OAc)3 as a reducing agent. Using this procedure, the asymmetric reductive amination of α-tetralone derivatives and indanone proceeds with >95% de. Lower diastereomeric excesses are observed for benzosuberone (16.7% de) and acetophenone (27.3% de). rac-21 gave (1′S,8′S,1(R)-25a (38% yield) and (1′R,8′S,1(R)-25b (44.5% yield) with greater than 52 and 78% de, respectively. Cleavage of the amino auxiliary of (1′S,8′S,1(R)-25a and of (1′R,8′S,1(R)-25b with lead(IV) tetraacetate and hydrolysis of the hydantoin ring yields the unprotected analogs of 4 and 5. The latter are transformed into the selectively protected target molecules 4 and 5 through standard protection procedures. The overall yield of the 17- and 18-step synthesis starting from 13 was 0.3% yield for each constrained lysine derivative.

Diastereoselective addition of grignard reagents to chiral 1,3- oxazolidines having a N-diphenylmethyl substituent

Chiral 1,3-oxazolidines having a diphenylmethyl group at the 3-position of the oxazolidine ring as a bulky substituent were synthesized. The reaction of Grignard reagents with the chiral 1,3-oxazolidines afforded the corresponding amines with very high di

Stereocontrolled addition of grignard reagents to chiral 1,3-oxazolidines having N-methoxybenzyl groups : Effect of N-substituent in diastereoselectivity

Chiral 1,3-oxazolidines having various N-methoxybenzyl groups were synthesized from (R)-phenylglycinol in three steps. The reactions of chiral 1,3-oxazolidines with Grignard reagents proceeded gently to give the corresponding chiral amines in quantitative yield and high diastereoselectivity. The best results regarding diastereoselectivity were achieved using a chiral 1,3-oxazolidine having N-2,4,6-trimethoxybenzyl moiety. These nitrogen functional groups could be easily removed from the chiral amines using TFA.

Asymmetric Synthesis of (1R,1'R)- and (1S,1'S)-Bis(1-arylethyl)amines by way of a Diastereoselective Addition to Chiral Imines and Oxaxolidines with Organometallic Reagents

The asymmetric synthesis of the bis(α-methylbenzyl)amines, (1R,1'R)- and (1S,1'S)-bis(1-arylethyl)amines 6, utilizing a diastereoselective reaction of chiral imines and oxazolidines derived from (R)-phenylglycinol with organometallic reagents, is describe

DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL IMINES AND 1,3-OXAZOLIDINES

The reaction of MeLi or MeMgBr with chiral aromatic imines and 2-aryl-1,3-oxazolidines derived from (R)-phenylglycinol afforded with good diastereoselectivity (R,R)-amines from imines, but the (R,S)-amines from 1,3-oxazolidines, respectively.

Enantioselective Synthesis of Primary Amines via Grignard Additions to Stereogenic N-(α-Phenyl-β-(benzyloxy)ethyl)nitrones

Addition of a wide range of Grignard to C-aryl- and C-alkyl-N-(α-phenyl-β-(benzyloxy)ethyl)nitrones (4-7) occurred with high diastereoselectivity (90:10 to 97:3 ratios) and good yields (56 - 97percent).Notable exceptions are allyl- and (o-methoxyphenyl)magnesium bromides (low selectivity but satisfactory yields) and isopropyl- and tert-butylmagnesium chlorides (high selectivity but 33 - 34percent yields) with C-phenylnitrone 4.The relative stereochemistry of hydroxylamine adducts 8a,b (from reaction of 4 with CH3MgBr) and 19a,b (from C-pentylnitrone 7 with MeMgBr) was provenby various correlations and/or by degradation to enantiomerically enriched amines.The other stereochemical assignments are based upon 1H NMR spectral and polarity correlations and/or by analogy to the two proven cases.The configuration of the major product can be rationalized by assuming that the Grignard reagents attack the nitrone face opposite to the pseudoequatorial N-(α-phenyl) group in a six-membered magnesium chelate (27 -> 28). 1H NMR spectral evidence indicates that a 1:1 complex of nitrone 4 and magnesium bromide exists in a chelated structure (29B) in CD2Cl2.Enantioselective syntheses of (S)-α-phenylethylamine (94percent ee) and (S)-2-heptylamine (82percent ee) were accomplished in five steps (33-39percent overall yields) from optically pure (S)-nitrones 4 and 7.

Diastereoselective Synthesis of Chiral Secondary Amines with Two Chiral Centers Directly Attached to the Nitrogen Atom

The synthesis of the amines 1a-f by hydrogenation of the corresponding imines 4a-f occurs with a diastereoselectivity ranging from 33percent to higher than 90percent.The absolute configurations of 1b-f have been determined by either X-ray analysis (1b and