C1CCCCC=1.[F:7][C:8]([F:29])([F:28])[CH2:9][CH2:10][CH2:11][CH:12]([NH:17]C(=O)OCC1C=CC=CC=1)[C:13]([OH:16])([CH3:15])[CH3:14].[ClH:30]>[Pd].C(O)C.C(OCC)C>[ClH:30].[NH2:17][CH:12]([CH2:11][CH2:10][CH2:9][C:8]([F:7])([F:28])[F:29])[C:13]([CH3:14])([OH:16])[CH3:15]Under argon, 319 mg (0.30 mmol, 10% pure) of palladium on activated carbon and 9.1 ml (90.0 mmol) of cyclohexene were added to 1.0 g (3.0 mmol) of rac-benzyl (7,7,7-trifluoro-2-hydroxy-2-methylheptan-3-yl)carbamate Example 101A in ethanol (21 ml), and the reaction mixture was stirred at reflux overnight. The mixture was filtered through a Millipore® filter and the filter cake was washed with ethanol. 3 ml (6.0 mmol) of 2 N hydrochloric acid in diethyl ether were added to the filtrate and the mixture was concentrated and dried under high vacuum. This gave 785 mg (111% of theory) of the target compound. The product was used without further purification for the next reaction.
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