Water → 3-((Tert-butoxycarbonyl)amino)propyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(Boc-amino)-propanol (10 g, 57.5 mmol) in dichloromethane (100 mL) was added triethylamine (11.6 g, 115 mmol) at 0° C., then methanesulfonyl chloride (7.9 g, 69 mmol) was dropwise added. The resulting mixture was stirred for 1 hour at 0° C., poured into water, and then extracted with dichloromethane for 3 times (100 mL for each time). The organic phases were combined, dried and concentrated to afford the product 3-(tert-butyloxycarbonylamino)propyl methanesulfonate (13.1 g, yield: 94%). The characterization of the resulting product was as follows: 1HNMR (400 MHz, CDCl3): δ=4.76 (s, 1H), 4.26 (t, J=6.4 Hz, 2H), 3.22-3.24 (m, 2H), 3.00 (s, 3H), 1.89-1.92 (m, 2H), 1.41 (s, 9H).

Provenance & Evidence