ChemicalBook CAS DataBase List （2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine..

（2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine.. synthesis

8synthesis methods

Product Name:（2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine..
CAS Number:942308-58-9
Molecular formula:C13H17NO4
Molecular Weight:251.28

13504-86-4 Synthesis

13504-86-4
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（2s，4s）-benzyl-4-hydroxy-2-（hydroxymethyl）pyrrolidine..

942308-58-9
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Yield:942308-58-9 100%

Reaction Conditions:

with boron dimethyl-trifluoro sulphide in tetrahydrofuran at 0 - 20; for 2.5 h;

Steps:

46

1-Benzyloxycarbonyl-cis-4-hydroxy-L-proline (10.03 g, 37.8 mmol) was introduced to a 200-mL pear-shaped flask, and while stirring the content under ice cooling, tetrahydrofuran (60 mL) was added to dissolve the compound. Then, a borane-dimethyl sulfide complex (2.0 M tetrahydrofuran solution) (37.8 mL, 75.6 mmol) was slowly added, and then the mixture was stirred for 2.5 hours at room temperature. The reaction solution was concentrated under reduced pressure, and poured onto ice water, and the mixture was extracted with ethyl acetate (200 mLx2). The combined organic layer was washed with saturated brine (200 mL), and then dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure, to obtain the title compound (9.93 g, q.y.) as an oily matter.

References:

EP1961750,2008,A1 Location in patent:Page/Page column 108