Triethylamine → (R)-N-(2-phenylpropyl)propane-2-sulfonamide

To a solution of 2-phenyl-propylamine HCl salt (1.0 g, 5.8 mmol), DMAP (35 mg, 0.3 mmol) and Et3N (1.77 g, 17.5 mmol) in DCM (25 mL) was added propane-2-sulfonyl chloride (1.25 g, 8.7 mmol) dropwise at 0° C. The mixture was stirred at r.t. for 16 h, and was then concentrated under vacuum. The residue was partitioned between EtOAc (100 mL) and H2O (10 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous Na2SO4, filtrated and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=2/1 to 1/1) to obtain the desired product (1.2 g, 86%) as a pale yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.30-7.32 (m, 2H), 7.18-7.24 (m, 3H), 3.90-3.94 (m, 1H), 3.30-3.35 (m, 1H), 3.18-3.22 (m, 1H), 2.99-3.04 (m, 1H), 2.91-2.95 (m, 1H), 1.27 (d, 3H, J=7.2 Hz), 1.25 (d, H, J=7.8 Hz), 1.22 (d, 1H, J=7.2 Hz).

1. concentrationwas then concentrated under vacuum
2. customThe residue was partitioned between EtOAc (100 mL) and H2O (10 mL)
3. customThe organic layer was separated
4. washwashed with brine (10 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltrated
7. concentrationconcentrated
8. customto give an oil residue
9. customThis residue was purified with silica gel column (Hexane/EtOAc=2/1 to 1/1)

ORD record

ord-3b0e97b9696448e195819d4c87ec5f59

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328125B2