Acetic Acid → (2-Amino-2-methylpropyl)dimethylsulfonium chloride hydrochloride

A solution of (2-(benzyloxycarbonylamino)-2-methylpropyl)dimethyl-sulfonium iodide (1.20 g, 3.03 mmol) in a mixture of water (25 mL), methanol (10 mL) and acetic acid (0.4 ml, 2 equiv, 6.06 mmol) was cooled in an ice bath for 5 min, then Ag2O (0.46 g, 0.65 equiv, 1.97 mmol) was added in one portion. The black suspension immediately changed to a cream color suspension and stirred for 30 min. This suspension was filtered through a pad of Celite® and the solid was washed with water (30 mL). The filtrate was acidified to ˜pH 2 with 6 N HCl and filtered through Celite® and the residue was washed with water (50 mL). The filtrate was concentrated on a rotovap to give a yellow oil. The crude hydrochloride salt was dissolved into water (20 mL) and 10% Pd/C (300 mg) was added to the reaction in one portion followed by 6 N HCl (1 mL, 2 equiv). The flask was sealed and degassed with vacuum and flushed with hydrogen from a balloon (3×). The reaction was stirred at room temperature for 20 h. The suspension was filtered through a pad of Celite® and the solid was washed with water (2×50 mL). The solution was concentrated in vacuo to a light yellow oil which upon repeated addition and evaporation of isopropyl alcohol (3×10 mL) provided the desired compound (0.62 g, quant). 1H NMR (D2O, 400 MHz): δ 1.41 (s, 6H), 2.51 (s, 2H), 2.98 (s, 2 H). LRMS (ESI−) for C6H16NS+ (134.1); Found: 134 (M+).

1. temperaturewas cooled in an ice bath for 5 min
2. filtrationThis suspension was filtered through a pad of Celite®
3. washthe solid was washed with water (30 mL)
4. filtrationfiltered through Celite®
5. washthe residue was washed with water (50 mL)
6. concentrationThe filtrate was concentrated on a rotovap
7. customto give a yellow oil
8. additionwas added to the reaction in one portion
9. customThe flask was sealed
10. customdegassed with vacuum
11. customflushed with hydrogen from a balloon (3×)
12. stirringThe reaction was stirred at room temperature for 20 h
13. filtrationThe suspension was filtered through a pad of Celite®
14. washthe solid was washed with water (2×50 mL)
15. concentrationThe solution was concentrated in vacuo to a light yellow oil which
16. additionaddition and evaporation of isopropyl alcohol (3×10 mL)

ORD record

ord-f88ce7939ad94985b466a8104c468404

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2