(1S,2S)-trans-1-Benzoyloxy-2-bromocyclohexane (CAS no.: 222851-77-6) could be produced through the following routes.

A. (S)-N-(N-tert-Butoxycarbonylprolyl)dihydroisoindole. A dry, 100-mL, two-necked flask equipped with a -coated magnetic stirring bar and a septum cap is charged with (S)-N-tert-butoxycarbonylproline (5.05 g, 23.5 mmol), dihydroisoindole (2.54 g, 21.3 mmol), and dichloromethane (25 mL) under an argon atmosphere. After cooling to 0 °C with the aid of an ice-water bath, a solution of dicyclohexylcarbodiimide (DCC, 5.1 g, 24.7 mmol) in dichloromethane (20 mL) is added and the reaction mixture is allowed to warm to room temperature while stirring overnight. The mixture is filtered through Celite, concentrated, and purified by column chromatography (ethyl acetate/hexanes:1/3) to afford (S)-N-(N-tert-butoxycarbonylprolyl)dihydroisoindole (4.1 g, 61%) as a white solid.

B. (S)-1-Methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine. A dry, 200-mL, three-necked, round-bottomed flask equipped with a Teflon-coated magnetic stirring bar, a reflux condenser, a septum cap, and an argon inlet is charged with lithium aluminum hydride (LAH, 0.96 g, 25.3 mmol) in THF (10 mL). After cooling to 0 °C with the aid of an ice-water bath, a solution of (S)-N-(N-tert-butoxycarbonylprolyl)dihydroisoindole (3.96 g, 12.5 mmol) in THF (15 mL) was added under an argon atmosphere. The cooling bath is removed and the reaction mixture is refluxed for 3 h. After cooling the mixture to 0 °C, the reaction is quenched carefully by the slow addition of saturated aqueous sodium sulfate (approx 5 mL). The liquid is decanted away from the precipitate, and the precipitate was washed with THF (2 × 20 mL). The combined liquid is dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (CH₂Cl₂/MeOH/Et₃N:95/5/1), to afford (S)-1-methyl-2- [(dihydroisoindol-2-yl)methyl]pyrrolidine (1.56 g, 58%).

C. (1S,2S)-trans-1-Benzoyloxy-2-bromocyclohexane. A 100-mL, two-necked flask equipped with a Teflon-coated magnetic stirring bar and a septum cap is charged with 1 g of molecular sieves 4 Å, and flame-dried under reduced pressure. After being allowed to warm to ambient temperature, the apparatus is flushed with argon. The flask is charged with (S)-1-methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine (65 mg, 0.28 mmol) in dichloromethane (5 mL), triethylamine (5.56 g, 55 mmol) in dichloromethane (15 mL), and racemic trans-2-bromocyclohexanol (17.91 g, 100 mmol) in dichloromethane (40 mL) by means of an oven-dried syringe and needle. After cooling to -78 °C by immersion in a dry-ice bath, benzoyl chloride (9.14 g, 65 mmol) in dichloromethane (20 mL) is added slowly over 30 min by means of an oven-dried syringe and needle. The solution is stirred for 3 h at -78 °C, and then quenched with a phosphate buffer (pH 7). The layers are separated and the aqueous layer extracted with diethyl ether (3 × 50 mL). The combined organic phase is washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The crude products are purified by column chromatography (ethyl acetate/hexanes:1/50) to give (1S, 2S)-trans-1-benzoyloxy-2-bromocyclohexane (14.25 g, 50%) and unreacted alcohol (1R, 2R)-trans-2-bromocyclohexanol (6.60 g, 37%).