Methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate → Methyl 5-aminobicyclo[3.2.1]octane-1-carboxylate

To a solution of methyl 5-(benzyloxycarbonylamino)bicyclo-[3.2.1]octane-1-carboxylate (10 g) in methanol (150 mL) was added 10% Pd/C (1 g) and the reaction mixture was stirred under H2 (1 atm) at room temperature overnight. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated. The residue was treated with aqueous HCl (2N, 200 mL) at 0° C. and then extracted with ethyl acetate (3×100 mL) to remove organic impurities. The aqueous phase was adjusted to pH 9-10 with Sat. Na2CO3 and extracted with dichloromethane/methanol (10/1, 3×100 mL). The combined organic layer was washed with water (100 mL) and brine (100 mL), dried over sodium sulfate and concentrated under reduced pressure to afford 2.98 g of methyl 5-aminobicyclo[3.2.1]octane-1-carboxylate as a yellow oil. ESI-MS m/z: 184 (M+H)+.

1. filtrationThe reaction mixture was filtered through a Celite pad
2. concentrationthe filtrate was concentrated
3. additionThe residue was treated with aqueous HCl (2N, 200 mL) at 0° C.
4. extractionextracted with ethyl acetate (3×100 mL)
5. customto remove organic impurities
6. extractionextracted with dichloromethane/methanol (10/1, 3×100 mL)
7. washThe combined organic layer was washed with water (100 mL) and brine (100 mL)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-2e030e6775aa487897c6083bdf80c0cd

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921370B2