(3R)-1-(tert-Butoxycarbonyl)-3-[(4-fluorobenzylthio)methyl]pyrrolidine → (3R)-3-[(4-Fluorobenzylthio)methyl]pyrrolidine

A solution of (3R)-1-(tert-butoxycarbonyl)-3-[(4-fluorobenzylthio)methyl]pyrrolidine (0.5422 g, 1.67 mmol) in 90% formic acid (5 ml) was stirred at room temperature for 23 h. The solvents were removed in vacuo and the residue was dissolved in dichloromethane (25 ml) and washed with 2N NaOH solution (10 ml). The aqueous layer was reextracted with more dichloromethane (25 ml) and the combined organic extracts were washed with saturated NaCl solution (10 ml), dried (Na2SO4) and evaporated in vacuo to leave 0.3903 g of the title compound as an oil. δH (360 MHz, CDCl3) 1.42 (1H, m), 1.94 (1H, m), 2.24 (1H, m), 2.45 (2H, m), 2.59 (1H, m), 2.92 (2H, m), 3.08 (1H, m), 3.69 (2H, s), 7.00 (2H, t, J=8.6 Hz), 7.25-7.29 (2H, m).

1. customThe solvents were removed in vacuo
2. dissolutionthe residue was dissolved in dichloromethane (25 ml)
3. washwashed with 2N NaOH solution (10 ml)
4. washthe combined organic extracts were washed with saturated NaCl solution (10 ml)
5. dry with materialdried (Na2SO4)
6. customevaporated in vacuo

ORD record

ord-e49b673b92f442ee967e7f4ba6891cf9

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05854268