Реакция #332980

Уравнение реакции

Boc-D-tert-leucine

HOBT

EDC

piperidine-4-carbonitrile

N,N-diisopropylethylamine

→

[(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester

Выход 97.3%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеthen quenched with 10% citric acid
2. 2
   Экстракцияextracted with EtOAc (2×)
3. 3
   ПромывкаThe combined organic layers were washed twice with 10% citric acid, twice with sat'd LiCl and once with brine
4. 4
   Сушкаthen dried over MgSO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated

Методика

A round-bottomed flask was charged with Boc-D-tert-leucine (2.5 g, 10.8 mmol), HOBT (4.2 g, 24.9 mmol), EDC (4.77 g, 24.9 mmol) and piperidine-4-carbonitrile (2.98 g, 27.0 mmol). Then added DMF (50 mL) followed by N,N-diisopropylethylamine (10.7 ml, 61.6 mmol). The yellow reaction mixture was stirred at room temperature overnight then quenched with 10% citric acid and extracted with EtOAc (2×). The combined organic layers were washed twice with 10% citric acid, twice with sat'd LiCl and once with brine then dried over MgSO4, filtered and concentrated to give 3.4 g (97%) of [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester as a beige foamy solid.

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