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CAS No. : | 192214-05-4 | MDL No. : | MFCD06410562 |
Formula : | C13H17NO3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ZRMWRJLLAVAFQP-GFCCVEGCSA-N |
M.W : | 235.28 | Pubchem ID : | 11042701 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H317-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With Jones reagent; In acetone; at 20.0℃; for 0.5h; | Step-3: Preparation of (R)- 1 -Benzyloxycarbonyl-pyrrolidine-3-carboxylic acid (X):To a solution of (R)-(1-benzyloxycarbonyl-pyrrolidin-3-yl)-methanol (IX, 80 gm, 0.34 mol) dissolved in acetone (800 ml) was added drop-wise under stirring Jones? reagent (200 ml, prepared by dissolving 53.4 gm Cr03 in a solution prepared by mixing 46 ml H2S04 and 140 ml water and fmal volume adjusted to 200 ml) at 20C tifi dark red colour persists of a solution and green coloured solid separates. The suspension was stirred for next 30 minutes. As the TLC (10% methanol in chloroform) showed complete conversion, isopropyl alcohol (100 ml) was added drop-wise to the reaction mixture, tifi green colour persists for 10 minutes. The suspension was filtered on the celite bed under suction and the solids were washed with fresh acetone (100 ml twice). The filtrate was evaporated under vacuum and to the residue was added saturated aqueous sodium bicarbonate solution (600 ml) tifi pH 8. The resultant mixture was extracted with ethyl acetate (400 ml) and layers were separated. Aqueous layer was adjusted to pH 2 by using 6N aqueous hydrochloric acid (125 ml). The reaction mixture was extracted with ethyl acetate (500 ml x 2) and dried over sodium sulfate. Evaporation of solvent afforded (R)- 1 -benzyloxycarbonyl-pyrrolidine-3-carboxylic acid (X) in 67 gm quantity as an oily syrup in 79% yield.Analysis:NMR: (CDC13):9.25 (br s, 1H), 7.25-7.35 (m, 5H), 5.13 (s, 2H), 3.62-3.71 (m, 2H), 3.52-3.54 (m, 1H), 3.43-3.49 (m, 1H), 3.07-3.10 (m, 1H), 2.09-2.18 (m, 2H).Mass (M-1): 248.1 for C13H15N04. |