Реакция #159295

Уравнение реакции

methyl 4-hydroxyadamantane-1-carboxylate

pyridine

triphosgene

→

1-(methoxycarbonyl)-4-adamantyl chloroformate

Растворители

CH2Cl2

CH2Cl2

Условия реакции

Обработка

1. 1
   Другое* The mixture was evaporated to dryness
2. 2
   Другоеthe residue was triturated with EtOAc (100 mL)
3. 3
   КонцентрированиеThe filtrate was concentrated

Методика

A stirred solution of methyl 4-hydroxyadamantane-1-carboxylate (1.01 g, 4.8 mmol) and pyridine (0.38 mL, 4.8 mmol) in CH2Cl2 (25 mL) was cooled in an ice bath and a solution of triphosgene (0.48 g, 1.6 mmol) in CH2Cl2 (10 mL) was added dropwise over 15 min. The ice bath was allowed to melt and the mixture was stirred for 3 h at rt.* The mixture was evaporated to dryness and the residue was triturated with EtOAc (100 mL). The filtrate was concentrated to afford 1-(methoxycarbonyl)-4-adamantyl chloroformate (1.19 g, 91%) as an oil. [* In some experiments the solution of 1-(methoxycarbonyl)-4-adamantyl chloroformate was used directly.]

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