Triethylamine → HCID 58386787, compound

To a solution of (3R,5R)-benzyl 3-hydroxy-5-methoxypiperidine-1-carboxylate (1 eq) in 40 mL of dichloromethane was added triethyl amine (3 eq) and methanesulfonyl chloride (1.5 eq) at 0° C. The reaction mixture was allowed to stir at room temperature for 2 hours. The crude mixture was diluted with 150 mL of EtOAc, washed with sat. aq. sodium bicarbonate, brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=1:1) to give the intermediate, which was dissolved in 15 mL of DMF. Sodium azide (3.3 eq) was added and the resulting suspension was stirred at 80° C. overnight. The reaction mixture was diluted with 150 mL of EtOAc, washed with water, brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=1:2) to yield (3S,5R)-benzyl 3-azido-5-methoxypiperidine-1-carboxylate (95%). LC/MS (m/z): 263.2 (MH+-28).

1. washwashed with sat. aq. sodium bicarbonate, brine
2. dry with materialdried over anhydrous MgSO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=1:1)
6. customto give the intermediate, which
7. stirringthe resulting suspension was stirred at 80° C. overnight
8. washwashed with water, brine
9. dry with materialdried over anhydrous MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=1:2)

ORD record

ord-4a70d61cc5164477964affe08a20afa7

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829193B2