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ChemicalBook CAS DataBase List cis-4-Hydroxy-D-proline
2584-71-6

cis-4-Hydroxy-D-proline synthesis

8synthesis methods
-

Yield:2584-71-6 253 mg

Reaction Conditions:

with water;sodium hydroxide in ethanol; for 2 h;

Steps:

(2R, 4R)-4-hydroxyproline(1):

A solution of 5a (600 mg, 2.41 mol) in ethanol (9 mL)was subjected to hydrogenation under 50 psi hydrogen pressure in presence of10% Pd(OH)2 (150 mg) for 3 h. The catalyst was filtered off and thesolution evaporated to dryness. Crude charged with 6 mL, 1M NaOH solution andstirred for 2 h. The reaction mass acidified with acetic acid to pH ~ 5 andpurified with Indion 225 H resin, product eluted in 5% aqueous ammonia. Productfraction evaporated to get solid, which was further purified with ethanol (5 mL)to afford 253 mg of with 80% yield.MP = 248-251 °C(decomposition), [α]D25 = +55.87° (c 1.0, H2O),lit.3, [α]D25 = +58.6° (c 0.65, H2O).1H NMR (400 MHz, D2O): δ ppm2.18-2.23 (m, 1H), 2.42-2.49 (m, 1H), 3.32 (dd, J = 3.9 Hz, 1H), 3.41 (d, J = 12.3 Hz, 1H), 4.16 (dd, J = 3.9 Hz, 1H), 4.53 (m, 1H).; 13CNMR (100 MHz, D2O): δ ppm 37.06,82.85, 59.59, 69.05, 174.43.; IR: 3213, 1633, 1564, 1433, 1383.; HRMS (ESI):Calcd for C5H8O3 (M-H)+ 130.0504, Found130.0501. MP = 248-251 °C (decomposition), [α]D25= +55.87° (c 1.0, H2O), lit.3, [α]D25= +58.6° (c 0.65, H2O).

References:

Gajare, Vikas S.;Khobare, Sandip R.;Malavika;Rajana, Nagaraju;Venkateswara Rao;Syam Kumar [Tetrahedron Letters,2015,vol. 56,# 24,p. 3743 - 3746] Location in patent:supporting information

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