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ChemicalBook CAS DataBase List T-BUTYL (2R,3R)-3-AMINO-2-HYDROXY-3-PHENYLPROPANOATE
135981-02-1

T-BUTYL (2R,3R)-3-AMINO-2-HYDROXY-3-PHENYLPROPANOATE synthesis

7synthesis methods
Benzenepropanoic acid, α-hydroxy-β-[[(1R)-1-phenylethyl](phenylmethyl)amino]-, 1,1-dimethylethyl ester, (αR,βR)-

151671-03-3
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T-BUTYL (2R,3R)-3-AMINO-2-HYDROXY-3-PHENYLPROPANOATE

135981-02-1
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Yield:135981-02-1 100%

Reaction Conditions:

with 10 wt% Pd(OH)2 on carbon;hydrogen in methanol at 20; under 3800.26 Torr; for 15 h;

Steps:

4.17 tert-Butyl (R,R)-2-hydroxy-3-amino-3-phenylproanoate 31

Pd(OH)2/C (27mg, 25% w/w) was added to a degassed solution of 14 (108mg, 0.292mmol, >99:1 dr) in MeOH (5mL) and the resultant mixture was stirred under H2 (5atm) at rt for 15h. The reaction mixture was then filtered through Celite (eluent MeOH) and concentrated in vacuo to give 31 as a colourless oil (55mg, quant, >99:1 dr);10a [α]23D[α]D23 -27.7 (c 1.0 in CHCl3); {lit.10a [α]23D[α]D23 -29.0 (c 0.5 in CHCl3)}; δH (400MHz, CDCl3) 1.33 (9H, s, CMe3), 3.42-3.47 (3H, br s, NH2, OH), 4.33-4.38 (2H, m, C(2)H, C(3)H), 7.21-7.36 (5H, m, Ph).

References:

Davies, Stephen G.;Fletcher, Ai M.;Frost, Aileen B.;Lee, James A.;Roberts, Paul M.;Thomson, James E. [Tetrahedron,2013,vol. 69,# 42,p. 8885 - 8898]

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