Hydrochloric Acid → 3-AzetidinecarboxaMide, 3-aMino-, Monohydrochloride

To a solution of 1-benzhydryl-3-benzylaminoazetidine-3-carboxylic acid amide (I-2A-1d; 1.83 g, 4.80 mmol) in methanol/methylene chloride was added excess 1 M HCl in diethyl ether (3.5 ml). After stirring for 10 minutes, the solvent was removed, in vacuo, and the resultant hydrochloride salt dissolved in 10:1 methanol/water (55 ml). After the addition of 20% Pd(OH)2 on carbon (50% water; 0.37 g), the mixture was placed on a Parr®) shaker and then reduced (50 psi H2) at room temperature for 23 hours. The reaction was diluted with methanol (50 ml), filtered through a 0.45 μM disk, and the disk rinsed with methanol (2×100 ml). The combined methanolic solutions were concentrated, in vacuo, and then triturated from diethyl ether to afford I-3A-6a (262 mg, 85%) as a tan solid: +APcI MS (M+1) 115.8; 1H NMR (400 MHz, CD3OD) δ 4.58 (d, J=13.3 Hz, 2H), 4.47 (d, J=13.3 Hz, 2H).

1. customthe solvent was removed, in vacuo
2. dissolutionthe resultant hydrochloride salt dissolved in 10:1 methanol/water (55 ml)
3. additionAfter the addition of 20% Pd(OH)2 on carbon (50% water; 0.37 g)
4. customat room temperature
5. customfor 23 hours
6. additionThe reaction was diluted with methanol (50 ml)
7. filtrationfiltered through a 0.45 μM disk
8. washthe disk rinsed with methanol (2×100 ml)
9. concentrationThe combined methanolic solutions were concentrated, in vacuo
10. customtriturated from diethyl ether
11. customto afford I-3A-6a (262 mg, 85%) as a tan solid

ORD record

ord-3019e61a7b0d46609544600eb435d068

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329658B2