ChemicalBook CAS DataBase List cis-4-Hydroxy-D-proline

cis-4-Hydroxy-D-proline synthesis

8synthesis methods

Product Name:cis-4-Hydroxy-D-proline
CAS Number:2584-71-6
Molecular formula:C5H9NO3
Molecular Weight:131.13

51-35-4

2584-71-6

General procedure for the synthesis of cis-4-hydroxy-D-proline using L-hydroxyproline as starting material: a synthetic route has been successfully developed for the other two stereoisomers in the pro4 monomer class. A controlled differential isomerization strategy [34] was employed to convert 30 g of trans-4-hydroxy-(L)-proline 5 into its diastereoisomer cis-4-hydroxy-(D)-proline 14 in 57% isolated yield. Further processing of the intermediate by the synthetic method described in Scheme 1 allowed the synthesis of two additional enantiomers of the pro4 structural unit class 3, pro4(2R,4R) and pro4(2R,4S) (see Scheme 3 for details).

2-(R)-CARBOETHOXY-4-(R)-HYDROXYPYRROLIDINE

132666-67-2
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2584-71-6
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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

51-35-4 Synthesis

51-35-4
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2584-71-6
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References

444313-67-1 Synthesis