反応 #44485

反応方程式

di-tert-butyl azodicarboxylate

solution

1-Cycloheptyl-4-hydroxymethyl-3,3-dimethyl-pyrrolidin-2-one

phenol

triphenyl phosphine

→

title compound

1-cycloheptyl-3,3-dimethyl-4-(phenoxymethyl)pyrrolidin-2-one

溶媒

Toluene

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The reaction mixture was partitioned between toluene and water
3. 3
   その他The organic phase was separated
4. 4
   その他solvent evaporated in vacuo
5. 5
   その他The crude reaction mixture
6. 6
   その他was purified by preparative reverse phase HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 um particle size)

実験手順

A solution of Example 3A (50 mg, 0.2 mmoles), phenol (23.5 mg, 0.25 mmoles), and triphenyl phosphine (85.8 mg, 0.33 mmoles) was stirred in anhydrous Toluene (1.25 mL). To the reaction, di-tert-butyl azodicarboxylate (76.9 mg, 0.33 mmoles) was added and heated to 80° C. for one hour. The reaction mixture was partitioned between toluene and water. The organic phase was separated and solvent evaporated in vacuo. The crude reaction mixture was purified by preparative reverse phase HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 um particle size) using a gradient of 20% to 100% acetonitrile:water (0.1% trifluoroacetic acid) over eighteen minutes at a flow rate of 40 mL/minute to provide the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 7.27-7.32 (m, 2H), 6.95-6.99 (m, 1H), 6.88-6.91 (m, 2H), 4.06-4.19 (m, 1H), 4.07 (dd, J=9.15, 5.65 Hz, 1H), 3.92 (t, J=8.77 Hz, 1H), 3.51 (dd, J=9.92, 7.63 Hz, 1H), 3.13 (dd, J=9.76, 7.78 Hz, 1H), 2.45 (qd, J=7.86, 5.72 Hz, 1H), 1.43-1.82 (m, 12H), 1.25 (s, 3H), 1.05 (s, 3H). MS (APCI+) m/z 316.2 (M+H)+.

出典