Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate → HCID 131719080, compound

Temperature

-78 °C

A solution of glycine benzaldehyde imine (10.2 g, 53 mmol) in 100 ml of THF was added dropwise to a cooled (-78° C.) and stirred solution of potassium t-butoxide (5.8 g, 52 mmol) in 300 ml THF over 20 min. After 15 min. a solution of Boc-4-(2-iodoethyl) piperidine (1-6) (18.2 g, 52 mmol) was added and stirring continued at -78° C. for 2 h. followed by standing at -20° C. for 18 h. After stirring 2 h. at r.t., the reaction mixture was concentrated to 50% of volume, poured into ice cold saturated NH4Cl and extracted with ether. The organic phase was washed with brine, dried (MgSO4) and the solvent evaporated. 1 g of the resulting oil was dissolved in 10 ml of methanol, cooled to 0° C. and 100 mg of sodium borohydride added in portions over 5 mins. After an additional 10 min., the reaction was concentrated, poured into water and extracted with ether. The organic extracts were washed with brine, dried (MgSO4) and solvent evaporated to give crude product purified by flash column chromatography (5:1→2:1 hexane:EtOAc) to afford 410 mg of 4-1.

1. waitby standing at -20° C. for 18 h
2. stirringAfter stirring 2 h. at r.t.
3. concentrationthe reaction mixture was concentrated to 50% of volume
4. additionpoured into ice cold saturated NH4Cl
5. extractionextracted with ether
6. washThe organic phase was washed with brine
7. dry with materialdried (MgSO4)
8. customthe solvent evaporated
9. dissolution1 g of the resulting oil was dissolved in 10 ml of methanol
10. temperaturecooled to 0° C.
11. addition100 mg of sodium borohydride added in portions over 5 mins
12. waitAfter an additional 10 min.
13. concentrationthe reaction was concentrated
14. additionpoured into water
15. extractionextracted with ether
16. washThe organic extracts were washed with brine
17. dry with materialdried (MgSO4) and solvent
18. customevaporated
19. customto give crude product
20. custompurified by flash column chromatography (5:1→2:1 hexane:EtOAc)

ORD record

ord-9d247d0eb93c49b3bdab0c3d5644953c

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05441952