Реакция #155404

Уравнение реакции

N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(S)-carboxylic acid methyl ester

imidazole

TBSCl

HCl

→

desired acid

Выход 87.1%

N-Boc-1(R)-amino-2(S)-tert-butyldimethylsilyloxy-cyclopentane-4(S)-carboxylic acid

Выход 87.1%

Растворители

DCM

isopropanol

chloroform

NaOH

Условия реакции

Обработка

1. 1
   Температураby heating at 40° C. for 1 hour
2. 2
   ТемператураThe reaction mixture was cooled to room temperature
3. 3
   Другоеwas quenched with H2O (3 mL)
4. 4
   ДругоеThe organic layer was separated
5. 5
   Концентрированиеwas concentrated to dryness
6. 6
   Другоеto yield a residue, which
7. 7
   ТемператураThe reaction was cooled to 0° C.
8. 8
   Другоеthe organic layer was separated
9. 9
   Сушкаdried over Na2SO4
10. 10
    Концентрированиеconcentrated to dryness

Методика

To a stirring solution of N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(S)-carboxylic acid methyl ester (0.622 g, 2.40 mmol) in DCM (1.9 mL) was added imidazole (0.164 g, 2.41 mmol), DMAP (0.047 g, 0.35 mmol) and TBSCl (0.363 g, 2.40 mmol) and the reaction was stirred at room temperature for 18 hours, followed by heating at 40° C. for 1 hour. The reaction mixture was cooled to room temperature, and was quenched with H2O (3 mL). The organic layer was separated and was concentrated to dryness to yield a residue, which was dissolved in isopropanol (6 mL) and 1M NaOH (2.9 mL), and the reaction was heated at 60° C. for 1 hour. The reaction was cooled to 0° C. and slowly acidified to pH 3 with 1M HCl (3 mL). After adding chloroform (18 mL), the organic layer was separated, dried over Na2SO4, and concentrated to dryness to yield the desired acid (0.75 g, 2.09 mmol, 87.1% yield).

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