(S)-3-Hydroxypyrrolidine synthesis
- Product Name:(S)-3-Hydroxypyrrolidine
- CAS Number:100243-39-8
- Molecular formula:C4H9NO
- Molecular Weight:87.12
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Yield:99.33 % ee
Reaction Conditions:
with hydrogenchloride in water;1,2-dichloro-ethane at 20 - 60; for 3 h;
Steps:
11
108 g of S-3-t-butoxy-pyrrolidine thus obtained was added to dichloroethane 300 mL. Thereafter, concentrated HCl 117 g (1.16 mol) was dropwisely added to the solution for 1 hour. The solution was stirred for 2 hours at 55-600C. The reaction mixture was cooled to room temperature and then water 50 g was added to the mixture. Organic layer was removed. The water layer was concentrated under reduced pressure. To the residue, isopropanol (500 mL) was added and then NaOH 46.83 g (1.16 mol) was added for 1 hour and stirred at room temperature for 5 hours. Solid phase inorganic material was filtered out. Concentration under reduced pressure gave 45.3 g of S-3-pyrrolidinol (overall two step yield 52%, chemical purity 99.26%, optical purity 99.33%ee).[101] 1H NMR (CDCl , 400MHz): δ 1.7 l(m, IH), 1.95(m, IH), 2.23(br s, 2H), 2.80~2.93(m, 3H), 3.13(m, IH), 4.39(m, IH) ppm.
References:
WO2009/11551,2009,A2 Location in patent:Page/Page column 15-16
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