反応 #307928

反応方程式

NaF

trimethylsilyl (2S,4R)—N-(chloroacetyl)-4-(trimethylsilyloxy)pyrrolidine-2-carboxylate

→

(2S,4R)—N-(chloroacetyl)-4-hydroxypyrrolidine-2-carboxylic acid

収率 92.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他at 215° C.
2. 2
   その他The reaction mixture was evaporated to dryness in vacuo
3. 3
   洗浄The resulting solid was washed with 100 ml of anhydrous ether
4. 4
   その他dried in vacuo

実験手順

Anhydrous HF with nitrogen gas was bubbled into a solution of trimethylsilyl (2S,4R)—N-(chloroacetyl)-4-(trimethylsilyloxy)pyrrolidine-2-carboxylate (4.70 g, 15.0 mmol) in 20 ml of acetonitrile in a Teflon container [HF was generated by heating 10 g (100 mmol) of NaF.HF at 215° C. in a Teflon® vessel and carried with nitrogen flow into the solution]. The reaction mixture was then stirred at room temperature for 15 h. The reaction mixture was evaporated to dryness in vacuo. The resulting solid was washed with 100 ml of anhydrous ether and dried in vacuo to yield 2.67 g (yield 92%) of (2S,4R)—N-(chloroacetyl)-4-hydroxypyrrolidine-2-carboxylic acid as a off-white solid: mp 123-124° C. (dec): 1H-NMR (D2O) δ 1.9-2.4 (m, 2H), 3.4-3.7 (m, 2H), 3.9-4.2 (m, 2H), 4.25-4.5 (m, 2H): 13C-NMR (CDCl3) δ 36.65, 41.84, 54.87, 58.36, 69.79, 168.22, 175.30: High Resolution Mass/ESI-APCI method; (M+H)+ 208.0369 (calcd 208.0371 for C7H11ClNO4); (M+Na)+ 230.0189 [calcd 230.0191 for (C7H10ClNO4+Na)].

出典