반응 #159308

반응 방정식

HCl

tert-butyl azetidin-3-ylmethylcarbamate

i-Pr2NEt

2-adamantyl chloroformate

CH2Cl2

→

title compound

수율 23.0%

2-adamantyl 3-((tert-butoxycarbonylamino)methyl)azetidine-1-carboxylate

수율 23.0%

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred overnight at rt
2. 2
   세척eluted with ether (20 mL)
3. 3
   기타The eluate was evaporated to dryness
4. 4
   기타the residue was purified by preparative HPLC

실험 절차

A vial was charged with tert-butyl azetidin-3-ylmethylcarbamate (25 mg, 0.12 mmol), i-Pr2NEt (31 μL, 0.17 mmol) and a flea stir bar. A solution of 2-adamantyl chloroformate in CH2Cl2 (1.5 mL, 17 mg mL−1, 0.12 mmol) was added. The mixture was stirred overnight at rt. A 10-mL ChemElut cartridge (Varian Inc. catalog number 12198007) was wetted with 5% aq HCl (5 mL) and allowed to stand for 5 min. The reaction mixture was applied to the cartridge and eluted with ether (20 mL). The eluate was evaporated to dryness and the residue was purified by preparative HPLC to afford the title compound (10 mg, 23%). 1H NMR (CDCl3) δ 1.42 (s, 9H), 1.5-2.0 (14H), 2.76 (m, 1H), 3.35 (m, 2H), 3.67 (m, 2H), 4.03 (m, 2H), 4.68 (m, 1H), 4.78 (s, 1H); LC-MS Method 1 tR=2.08 min, m/z=387, 365, 309.

출처