Benzyl chloroformate → HCID 89525607, compound

Ethyl (3-aminotetrahydro-2H-pyran-3-yl)acetate (Preparation 32, 1.33 g, 7.109 mmol), benzyl chloroformate (1.53 g, 8.53 mmol) and N,N-diisopropylethylamine (3.72 mL, 21.3 mmol) were stirred in anhydrous acetonitrile (30 mL) for 18 hours at room temperature. The reaction was concentrated in vacuo then partitioned between ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with heptane:ethyl acetate:methanol (100:0:0-0:90:10). The oil isolated was then dissolved in methanol (10 mL) and a 1M aqueous solution of sodium hydroxide (10 mL) and heated to 75° C. for 18 hours. The methanol was removed in vacuo and the mixture partitioned between dichloromethane (10 mL) and water. The aqueous layer was acidified with 2M aqueous hydrogen chloride and extracted with dichloromethane (4×10 mL). The organic layer was dried over MgSO4 to afford the title compound as a oil (0.6 g, 29% yield over 2 steps).

1. concentrationThe reaction was concentrated in vacuo
2. customthen partitioned between ethyl acetate and water
3. dry with materialThe organic layer was dried over MgSO4
4. concentrationconcentrated in vacuo
5. customThe residue was purified by silica gel column chromatography
6. washeluting with heptane:ethyl acetate:methanol (100:0:0-0:90:10)
7. customThe oil isolated
8. customThe methanol was removed in vacuo
9. customthe mixture partitioned between dichloromethane (10 mL) and water
10. extractionextracted with dichloromethane (4×10 mL)
11. dry with materialThe organic layer was dried over MgSO4

ORD record

ord-408053db516f465399a25b5dbdba8f1e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079878B2