反应详情

To a solution of (2S-trans)-4-cyclohexyl-2-pyrrol idinemethanol(45 g) in tetrahydrofuran (400 ml) was added potassium carbonate solution (18.7 g, 120 ml water and cooled to -2° C. (Benzyloxy)carbonyl chloride (37.7 ml) was added dropwise to the well stirred reaction mixture, keeping the inside temperature between -2° and 0° C. After the addition (20 minutes), the reaction mixture was stirred for 15 minutes at 0° C. and poured into crushed ice and water (500 ml). The organic layer was separated after saturation with sodium chloride and the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic phase was washed with 5% hydrochloric acid (2×100 ml), water (1×100 ml) and brine (1×100 ml). Evaporation of the solvents after drying over anhydrous sodium sulfate furnished a colorless thick oil, 78.1 g. TLC showed a single spot at Rf =0.7 with very faint shadow at origin and at solvent front (silica gel, ethyl acetate-hexane, 4:1, UV and iodine). [α]D =-21.0°.

1. additionwas added dropwise to the well
2. customreaction mixture
3. customthe inside temperature between -2° and 0° C
4. additionAfter the addition (20 minutes)
5. stirringthe reaction mixture was stirred for 15 minutes at 0° C.
6. additionpoured
7. customThe organic layer was separated after saturation with sodium chloride
8. extractionthe aqueous phase was extracted with ethyl acetate (3×100 ml)
9. washThe combined organic phase was washed with 5% hydrochloric acid (2×100 ml), water (1×100 ml) and brine (1×100 ml)
10. customEvaporation of the solvents
11. dry with materialafter drying over anhydrous sodium sulfate
12. customfurnished a colorless thick oil, 78.1 g
13. custom[α]D =-21.0°