p-Toluenesulfonic acid → HCID 86018577, compound

The (R)-3-hydroxypyrrolidine-1-carbaldehyde (31 g) was treated with dihydropyran (36.8 ml) and p-toluenesulphonic acid (1 g). The mixture was stirred at room temperature for approximately one hour, during which time the colour changed from yellow to dark purple. GC analysis showed the reaction was complete. The reaction was quenched by addition of saturated sodium bicarbonate solution (90 ml). The aqueous phase was extracted with DCM (3×90 ml). The combined organic phase was washed with saturated sodium chloride solution (90 ml), then dried over MgSO4 and concentrated at below 30° C. The product, 3-(tetrahydropyran-2-yloxy)pyrrolidine-1-carbaldehyde, was obtained in 100% yield, 54.5 g. GC analysis showed two adjacent peaks, RT 14.45 and 14.83 min, 49.7 and 47.1% respectively. δH (CDCl3) 8.22 and 8.27 (1H, 2×s), 4.60-4.75 (1H, m), 4.35-4.50 (1H, m), 3.80-3.95 (1H, m), 3.40-3.70 (5H, m), 1.40-2.20 (8H, m).

1. customThe reaction was quenched by addition of saturated sodium bicarbonate solution (90 ml)
2. extractionThe aqueous phase was extracted with DCM (3×90 ml)
3. washThe combined organic phase was washed with saturated sodium chloride solution (90 ml)
4. dry with materialdried over MgSO4
5. concentrationconcentrated at below 30° C

ORD record

ord-83271084f9fc4da0ba46c20d775db933

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07482452B2