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

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

7synthesis methods

Product Name:T-BUTYL (2R,3R)-3-AMINO-2-HYDROXY-3-PHENYLPROPANOATE
CAS Number:135981-02-1
Molecular formula:C13H19NO3
Molecular Weight:237.29

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)}; δ_H (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).