Water → HCID 25176288, compound

Temperature

60 °C

[(S)-1-((S)-7-Fluoro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-3-methyl-piperidin-3-yl]-methanol (2.5 g, 8.5 mmol) in tetrahydrofuran (10 ml) was added slowly to a mixture of sodium hydride, 60% in oil (1.354 g, 33.9 mmol) and tetrahydrofuran (15 ml). The reaction mixture was heated at 60° C. for 2 hours after the mixture was cooled down and iodomethane (0.685 ml, 11.0 mmol) in tetrahydrofuran (3 ml) was added. The mixture was stirred at RT for 1 hour, water (25 ml) was added carefully and the mixture was extracted twice with ethyl acetate. The combined ethyl acetate layers were evaporated to dryness. Ethyl acetate (20 ml) was added to the evaporation residue and was made acidic with aq HCl. The layers were separated and the water layer was made basic with aq NaOH and extracted twice with ethyl acetate. The combined ethyl acetate layers were evaporated to dryness to yield 2.34 g (89%) of the title compound.

1. temperaturewas cooled down
2. extractionthe mixture was extracted twice with ethyl acetate
3. customThe combined ethyl acetate layers were evaporated to dryness
4. additionEthyl acetate (20 ml) was added to the evaporation residue
5. customThe layers were separated
6. extractionextracted twice with ethyl acetate
7. customThe combined ethyl acetate layers were evaporated to dryness

ORD record

ord-c76a5ac9828842a9946cd0266a1649bd

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697723B2