2-Amino-3-phenyl-l-propanol

FIGURE 1.54 HPLC chromatogram of 2-amino-3-phenyl-l-propanol generated by cleavage of its t-BOC derivative with trifluoroacetic acid and clean-up on strata-X-C. 

Methods of Preparation. Two methods for the synthesis of 4-benzyloxazolidine-2-thione from 2-amino-3-phenyl-l-propanol (phenylalaninol) have been described. The appropriate amino alcohol is readily prepared from (/ )-phenylalanine or (. -phenylalanine by reduction with sodium borohydride and iodine in THF. Exposure of phenylalaninol to carbon disulfide and aqueous sodium carbonate for 15 min at 100 °C provided 4-benzyloxazolidine-2-thione in 63% yield (eq 1). Alternatively, the treatment of the amino alcohol with thiophosgene and triethy-lamine in dichloromethane for 30 min at 25 °C provided 95% of the oxazolidinethione (eq 2) The former method often results in the oxazolidinethione contaminated with varying amounts of the corresponding thiazolidinethione. 

A mixture consisting of 3-amino-3-phenyl-l-propanol (6.6 mmol), 4-chloro-2-fluorobenzonitrile (6.4 mmol) and 1.2 ml /V,/V-diisopropylcthylamine was heated 5 hours at 140°C then cooled. The material was purified by chromatography with... 

C9H12S 4-ethyl-(1 -thiaethyl)-benzene. .. 505.76 45.490 2 17310 C9H13NO L(-)-2-amino-3-phenyl-1-propanol 3182-95-4 459.35 39.993 2... 

Dimethyl sulfoxide Methyl sulfoxide (8) Methane, sulfinylbis- (9) (67-68-5) Triethylamine (8) Ethanamine, N,N-diethyl- (9) (121-44-8) (S)-2-Amino-3-phenyl-1 -propanol 1-Propanol, 2-amino-3-phenyl-, L- (8) Benzenepropanol, 2-amino-, (S)- (9) (3182-95-4)... 

L-2-Amino-3-phenyl-propanoll(l Zu einer Losung von 3,5 g (92 mMol) Natriumboranat in 50 ml 50%igem Athanol wird unter Riihren eine Losung von 5 g (22 mMol) L-Phenyl-alanin-athylester-Hydrochlorid in 50 ml... 

Allyl prolinate, 292 (lS,2S)-2-Amino-3-methoxy-l-phenyl-1-propanol, 17... 

The irradiation of phenyl-2-methyltricyclo[3.3.1.1]dec-2-yl methanone 54a (Scheme 37) included in faujasite was carried out in presence of chiral inductors. The maximum enantioselectivity obtained using the chiral inductor approach was 32% ee both with (— )-pseudoephedrine and with ( + )-2-amino-3-methoxy-l-phenyl-1-propanol [302], Similar studies were done for l-(4-fluorophenyl)-2 methyltricyclo[3.3.1. l]dec-2-yl methanone 54b. The maximum enantioselectivity obtained in this case was 30% ee with (— )-pseudoephedrine. 

Underivatized amino acids form complexes with copper(II). A variety of copper(II)-trapped phases have been developed for the enantiosepara-tion of amino acids. N-Salicylidene-(J )-2-amino-l,2-6is(2-buto Q -5-fe/t-bu(yl-phenyl)-3-phenyl-l-propanol was coated on an octadecyl-bonded silica gel column and copper sulfate solution was used as the eluent. The structure was constructed using the Molecular Editor program and optimized by MM2 calculations. The optimization was performed as the energy change was less than 10 kcal mol. The molecular weight of the chiral phase was 1449, and the final and van der Waals energies were 77.04 and —8.77 kcal mol, respectively. 

Figure 8.10 Structure of the binuclear Cu(n) derivative of JV-salicylidene-(i )-2-amino-l,l-/ /s(2-butO)g -5-tert-butylphenyl)-3-phenyl-l-propanol. White, light-gray, dark-gray, black, and gray balls, represent hydrogen, carbon, nitrogen, ojygen, and copper, respectively.

B. 2-(N-Benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propanol, 3. A mixture of 2 (16.7 g, 50 mmol), benzyl chloride (6.90 mL, 60 mmol) (Note 1), tetrabutylammonium iodide (200 mg) (Note 1) and potassium carbonate (8.4 g, 60 mmol) in acetonitrile (100 i L) is heated under reflux for 17 hr (Note 4). The cooled mixture is filtered and the salt is washed with diethyl ether (100 mL). The combined organic layers are concentrated and the residue is crystallized from dichloromethane (25 mL) and hexane (100 mL) to give 3 (17.0 g. 80%) (Notes 5, 6). 

Brunner et al. reported core-functionalised dendrimer metal catalysts ("dendri-zyme ) for use in enantioselective catalysis [lb, 10, 11]. Optically active dendrimer ligands were used, for example for the reaction of styrene with ethyl diazoacetate in a Cu(I)-catalysed enantioselective cyclopropanation. The starting compound for the preparation of these ligands was L-aspartic acid. However, (IS,2 S)-2-amino-1-phenyl-1,3-propanol can also serve as reactant for the synthesis of optically active dendrimer ligands. 

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