(1R,2S)-2-methylcyclohexan-1-ol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 4 ml of tetrahydrofuran was suspended 0.12 g of sodium hydride (60% in oil), to which 1 ml of a tetrahydrofuran solution containing 0.28 g of cis-2-methylcyclohexanol was slowly added dropwise with stirring at 0° C. The mixture was stirred at 0° C. for 10 minutes, to which 1 ml of a tetrahydrofuran solution containing 0.3 g of 4,6-dichloropyrimidine was added at 0° C., followed by further stirring at room temperature for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with t-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.12 g of 4-chloro-6-(cis-2-methylcyclohexyloxy)pyrimidine. was slowly added dropwise was added at 0° C. by further stirring at room temperature for 3 hours extracted three times with t-butyl methyl ether washed with water dried over anhydrous magnesium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 4 ml of tetrahydrofuran was suspended 0.12 g of sodium hydride (60% in oil), to which 1 ml of a tetrahydrofuran solution containing 0.28 g of cis-2-methylcyclohexanol was slowly added dropwise with stirring at 0° C. The mixture was stirred at 0° C. for 10 minutes, to which 1 ml of a tetrahydrofuran solution containing 0.3 g of 4,6-dichloropyrimidine was added at 0° C., followed by further stirring at room temperature for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with t-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.12 g of 4-chloro-6-(cis-2-methylcyclohexyloxy)pyrimidine. was slowly added dropwise was added at 0° C. by further stirring at room temperature for 3 hours extracted three times with t-butyl methyl ether washed with water dried over anhydrous magnesium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethvl (Z)-2-hydroxyimino-3-oxobutyrate (1.59 g) was alkylated with cis-2-methylcyclohexan-1-ol (1.71 g) as described in Example 4, method 3. The pure title compound was otained as a pale yellow oil (0.506 g). (Found: M+, 256.1552. C13H21NO4 requires M 256.1549); νmax (film) 1745, 1695 and 1595 cm-1 ; δH (CDCl3) 1.02 (3H, d, J 6 Hz), 1.35 (3H, t, J 7 Hz), ca 1.2-2.3 (9H, m), 2.40 (3H, s), 3.95 (1H, m) and 4.42 (2H, q, J 7 Hz).