Hydrochloric Acid → 3-(ethylamino)-3-Azetidinecarboxamide hydrochloride

Alternatively, a solution of 1-benzhydryl-3-ethylaminoazetidine-3-carboxylic acid amide (I-2A-1g; 9.2 g, 30 mmol) in methanol (150 ml) at 0° C. was added 1 M HCl in ether (75 ml, 75 mmol). The mixture was concentrated to ⅔ volume to remove the ether, in vacuo, and then methanol was added to bring the reaction volume to 150 mL. This was repeated a second time. After the addition of 20% Pd(OH)2 on carbon (50% water; 2.3 g), the mixture was placed on a Parr® shaker and then reduced (45 psi H2) at room temperature overnight. The mixture was diluted with methanol (350 ml) filtered through Celite®, rinsing with additional methanol. The methanol fractions were filtered through a 0.45 μm filter disk, and then concentrated under reduced pressure to give a solid residue that was triturated from diethyl ether, collected by vacuum filtration, washed with ether and then dried, in vacuo, to afford I-(13A-9)f (6.3 g, 91%) as a tan solid.

1. concentrationThe mixture was concentrated
2. customto remove the ether
3. additionin vacuo, and then methanol was added
4. additionAfter the addition of 20% Pd(OH)2 on carbon (50% water; 2.3 g)
5. customat room temperature
6. customovernight
7. additionThe mixture was diluted with methanol (350 ml)
8. filtrationfiltered through Celite®
9. washrinsing with additional methanol
10. filtrationThe methanol fractions were filtered through a 0.45 μm
11. filtrationfilter disk
12. concentrationconcentrated under reduced pressure
13. customto give a solid residue that
14. customwas triturated from diethyl ether
15. filtrationcollected by vacuum filtration
16. washwashed with ether
17. customdried, in vacuo
18. customto afford I-(13A-9)f (6.3 g, 91%) as a tan solid

ORD record

ord-b2ddce0df94046419f94dd93b8514249

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129239B2