Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2S)-2-[(4-bromophenyl)(cyclohexyl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

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Reaction Steps

To a solution of (4-bromophenyl)(cyclohexyl)methyl 2,2,2-trichloroethanimidoate of step 2 (4.18 mmol, 1.73 g) in CH2Cl2 (15 mL) was added (2S)-N-(cyanomethyl)-2-hydroxy-4-methylpentanamide from Step 1, Example 67 (4.18 mmol, 0.71 g) and then PPTS (0.42 mmol, 0.105 g). The mixture was stirred at r.t. for 72 h. A red solution resulted. The mixture was diluted with EtOAc and washed with NaHCO3. The organic extract was dried (anhyd. MgSO4) and concentrated under reduced pressure to give an oil. Chromatography gave the less polar diastereomer and the more polar isomer.

Provenance & Evidence