Reaktion #58603

Reaktionsgleichung

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

Ausbeute 62.0%

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

Ausbeute 62.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePurification by ion exchange ion exchange chromatography

Vorschrift

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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