Trifluoroacetic acid → HCID 65991607, compound

Tert-butyl 3-(aminomethyl)-1-azetidinecarboxylate (J. Med. Chem., (2001) 44:94-104) (441 mg, 2.35 mmol) was dissolved in CH2Cl2 (2 mL) and TFA (1.5 mL) and the mixture was stirred for 2 hours at room temperature. The volatiles were removed under reduced pressure and the residue was dissolved in dry MeOH (5 mL). Solid NaHCO3 was added (˜500 mg) and the mixture was stirred for 17 hours. MeOH was removed, CH2Cl2 (50 mL) was added and the mixture was filtered through a plug of Celite. The filtrate was concentrated and the residue was dissolved in DMF (15 mL). DIPEA (0.817 mL, 4.70 mmol) and 2-nitrobenzenesulfonyl chloride (580 mg, 2.58 mmol) were added and the mixture was stirred for 2 hours. The mixture was concentrated and the residue was purified by column chromatography on silica gel (100% EtOAc) to provide [1-(2-nitro-benzenesulfonyl)-azetidin-3-yl]-methanol (167 mg, 26%). 1H NMR (CDCl3) δ 2.73-2.80 (m, 1H), 3.76 (dd, 2H, J=5.4, 5.7 Hz), 3.90 (dd, 2H, J=5.7, 8.1 Hz), 4.17 (dd, 2H, J=8.1, 8.1 Hz).

1. customThe volatiles were removed under reduced pressure
2. dissolutionthe residue was dissolved in dry MeOH (5 mL)
3. additionSolid NaHCO3 was added (˜500 mg)
4. customMeOH was removed
5. additionCH2Cl2 (50 mL) was added
6. filtrationthe mixture was filtered through a plug of Celite
7. concentrationThe filtrate was concentrated
8. dissolutionthe residue was dissolved in DMF (15 mL)
9. stirringthe mixture was stirred for 2 hours
10. concentrationThe mixture was concentrated
11. customthe residue was purified by column chromatography on silica gel (100% EtOAc)

ORD record

ord-f7865eb4f1c34d4ab6f6b5c5db4bdf57

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07501518B2