ChemicalBook CAS DataBase List (+)-O-METHYL-L-PHENYLALANINOL HYDROCHLORIDE

(+)-O-METHYL-L-PHENYLALANINOL HYDROCHLORIDE synthesis

9synthesis methods

Product Name:(+)-O-METHYL-L-PHENYLALANINOL HYDROCHLORIDE
CAS Number:64715-81-7
Molecular formula:C10H16ClNO
Molecular Weight:201.69

(S)-N-[1-(Methoxymethyl)-2-phenylethyl]acetamide

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(+)-O-METHYL-L-PHENYLALANINOL HYDROCHLORIDE

64715-81-7
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Yield:64715-81-7 0.1%

Reaction Conditions:

with hydrogenchloride in water; for 24 h;Reflux;

Steps:

Compound (S)-5

General procedure: Compound (S)-4 (14.0g, 67.6mmol) was refluxed in 6N HCl (90mL) for 24h. The solvent was evaporated under reduced pressure to obtain compound (S)-5 (13.6g) as a white solid in an almost quantitative yield. Mp=122-124°C; [α]_D²⁰ -13.3 (c 1.20, CH₃OH); ¹H NMR (400MHz, DMSO-d₆) δ 8.45 (s, 2H), 7.34 (t,J=7.2Hz, 2H), 7.30-7.26 (m, 3H), 3.44-3.41 (m, 2H), 3.33 (dd, J=10.4, 6.0Hz, 1H), 3.27 (s, 3H), 3.08 (dd, J=13.2, 4.8Hz, 1H), 2.83 (dd, J=13.2, 9.2Hz, 1H), 2.59 (t, J=4.8Hz, 1H); ¹³C NMR (100MHz, DMSO-d₆) δ 136.41, 129.17 (2C), 128.59 (2C), 126.79, 70.08, 58.43, 51.54, 34.91; HRMS calcd for C₁₀H₁₆NO [M+H]⁺ 166.1226, found 166.1227.

References:

Pan, Xuan;Liu, Zhanzhu [Tetrahedron,2014,vol. 70,# 31,p. 4602 - 4610]