Hydrogen Peroxide → HCID 86757490, compound

A solution of 0.590 g (2.02 mmol) of 1-benzyl-4-(3-phenylpropyl)-1,2,3,6-tetrahydropyridine and 4.4 mL of a 1M solution of BH3.THF in THF in 5 mL of THF was heated under reflux for 1 h. The mixture was cooled to rt, and 5 mL 1N NaOH and 5 mL 30% H2O2 were added and stirring was continued for 0.5 h. The mixture was partitioned between 75 mL of ether and 25 mL of H2O. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue and 2 mL of ethanolamine were combined in 2 mL of methanol and heated under reflux for 1 h. The mixture was cooled to rt and partititioned between 100 mL of ether and 50 mL of sat'd NaCl solution. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 2:1) to give 1-benzyl (trans)-3-hydroxy-4-(3-phenylpropyl)piperidine. Removal of the benzyl protecting group was achieved under standard conditions.

1. temperatureunder reflux for 1 h
2. customThe mixture was partitioned between 75 mL of ether and 25 mL of H2O
3. washThe combined organic fractions were washed with sat'd NaCl solution
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationthe filtrate was concentrated
7. temperatureheated
8. temperatureunder reflux for 1 h
9. temperatureThe mixture was cooled to rt
10. washThe combined organic fractions were washed with sat'd NaCl solution
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationthe filtrate was concentrated
14. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 2:1)

ORD record

ord-c5cc45bfd45541a794f7ca210b23326d

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303593B1