Реакция #1747880

Уравнение реакции

methyl ester

(4R)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-hexanoic Acid Methyl Ester

potassium borohydride

→

alcohol

(3S,4R)-4-Benzyloxycarbonylamino-3-hydroxy-5-methylhexanoic Acid Methyl Ester

Растворители

MeOH

Условия реакции

Обработка

1. 1
   Температураwarmed to −20° C. for 30 min
2. 2
   workup.WAITto 0° C. for 10 min
3. 3
   ДругоеThe reaction was quenched with acetic acid to pH 7
4. 4
   Экстракцияextracted with CH2Cl2 (3×50 mL)
5. 5
   ПромывкаThe organic layer was washed with NaHCO3 (50 mL, sat), NaCl (50 mL, sat)
6. 6
   Сушкаdried (Na2SO4)
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated

Методика

To a solution of methyl ester 11 (2.8 g, 9.15 mmol) in HPLC MeOH (30 mL), cooled to −78° C., potassium borohydride (1.72 g, 32 mmol) was added in portions. The reaction mixture was stirred at −78° C. for 10 min, warmed to −20° C. for 30 min and then to 0° C. for 10 min. The reaction was quenched with acetic acid to pH 7 and extracted with CH2Cl2 (3×50 mL). The organic layer was washed with NaHCO3 (50 mL, sat), NaCl (50 mL, sat), dried (Na2SO4), filtered and evaporated. The alcohol 12 was obtained as a colorless oil (2.7 g, 98%) and used directly in the next step. 1H-NMR (500 MHz, CDCl3): 0.87 (d, J=6.7 Hz, 3H), 0.94 (d, J=6.7 Hz, 3H), 2.10-2.19 (m, 1H), 2.47 (dd, J=16.7 and 9.1 Hz), 2.58 (dd, J=16.7 and 2.9 Hz, 1H), 3.11-3.20 (m, 1H), 3.56-3.63 (m, 1H), 3.68 (s, 3H), 3.90-3.98 (m, 1H), 4.64 (d, J=7.9 Hz, 1H), 5.09 (s, 2H), 7.30-7.39 (m, 5H).

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