반응 #307928

반응 방정식

NaF

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

→

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

수율 92.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타at 215° C.
2. 2
   기타The reaction mixture was evaporated to dryness in vacuo
3. 3
   세척The resulting solid was washed with 100 ml of anhydrous ether
4. 4
   기타dried in vacuo

실험 절차

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)].

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