Methanesulfonyl chloride → HCID 67492269, compound

Methanesulfonyl chloride (120 μL, 1.55 mmol) and DIPEA (187 μL, 1.07 mmol) were added to a solution of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (200 mg, 1.01 mmol) in DCM (20 mL) and the reaction mixture stirred at ambient temperature for 17 h, then partitioned between EtOAc and water. The organic layer was separated and washed with brine, then dried (MgSO4) and concentrated in vacuo to give (1S,4S)-5-methanesulfonyl-2,5-diazabicyclo[2.2.1]-heptane-2-carboxylic acid tert-butyl ester. TFA (3 mL) was added to a solution of (1S,4S)-5-methanesulfonyl-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester in DCM (10 mL) and the mixture stirred at ambient temperature for 30 min. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge (10 g); the cartridge was washed with MeOH before the desired product was eluted using 2 M NH3 in MeOH. The product was collected and concentrated in vacuo to afford the title compound as a white solid (170 mg, 96%). 1H NMR (CDCl3, 400 MHz) δ 4.37 (d, J=2.0 Hz, 1 H); 3.83 (d, J=2.0 Hz, 1 H); 3.41 (dd, J=9.2, 2.19 Hz, 1 H); 3.25 (d, J=9.2 Hz, 1 H); 3.20 (d, J=10.3 Hz, 1 H); 3.01 (dd, J=10.3, 2.14 Hz, 1 H); 2.89 (s, 3 H); and 1.79 (bs, 2 H)

1. custompartitioned between EtOAc and water
2. customThe organic layer was separated
3. washwashed with brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo

ORD record

ord-5dcaee1f09944ed59bd52044c594890c

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394796B2