Реакция #58603

Уравнение реакции

39

4-Fluoro[1,1′-biphenyl]-2-yl-4-methyl-2-[4-(phenylmethyl)morpholin-2-yl]pentan-2-ol

α-chloroethyl chloroformate

Hünig's base

→

40

Выход 62.0%

1-(4-Fluoro[1,1′-biphenyl]-2-yl)-4-methyl-2-morpholin-2-ylpentan-2-ol hydrochloride

Выход 62.0%

Растворители

DCM

Условия реакции

Обработка

1. 1
   ДругоеPurification by ion exchange ion exchange chromatography

Методика

40 is prepared from 39 (1.31 g, 2.92 mmol), α-chloroethyl chloroformate (0.9 mL) and solid supported Hünig's base (1.64 g) in anhydrous DCM (30 mL) following General Procedure 3. Purification by ion exchange ion exchange chromatography gives the free base of 40 as a viscous oil (0.71 g, 62%). After further purification using UV-guided preparative LCMS, the hydrochloride salt 40 (0.451 g, 39%) is obtained following General Procedure 4. MW 393.95; C22H28FNO2. HCl; 1H NMR (DMSO-d6): δ 9.16 (1H, s), 8.98 (1H, s), 7.44-7.32 (4H, m), 7.23-7.06 (4H, m), 3.83 (1H, dd, 12 Hz, 3 Hz), 3.59-3.50 (3H, m), 3.18 (1H, d, 12.5 Hz), 3.08 (1H, d, 12.5 Hz), 2.92-2.67 (4H, m), 1.54-1.40 (1H, m), 1.03 (1H, dd, 14.5 Hz, 5 Hz), 0.88 (1H, dd, 14.5 Hz, 6.5 Hz), 0.74 (3H, d, 6.5 Hz), 0.67 (3H, d, 6.5 Hz); LCMS: (12 minute method) m/z 358 [M−HCl+H]+ RT 5.47 min.

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