P-Toluenesulfonamido -2-Pentanol

Submitted by huGEMO Herranz and K Barry Sharpless Checked by Rita Locher, Thomas Weller, and Dieter Seebach [Pg.85]

Caution Because of the volatility and toxic nature of OsO, these reactions should be carried out in a well ventilated hood. [Pg.85]

cis-2-p-(Toluenesulfonamido)cyclohexanol. A 1-L, three-necked, round-bottomed flask is equipped with an efficient mechanical stirrer, thermometer, and reflux condenser. The flask is charged with 8.2 g (0.1 mol) of cyclohcxcnc (Note 1), 250 mL of reagent grade chloroform (Note [Pg.85]

After 10 hr at 55-60°C, 14 2 g (0 1 mol) of sodium sulfite (Note 6) IS added and the mixture is refluxed for 3 hr The hot reaction mixture (Note 7) IS transferred to a 1-L separatory funnel and allowed to stand for 10 min The organic layer is collected in a 500-mL, round-bottomed flask The aqueous layer is extracted once with 25 mL of CHCI3 which IS then combined with the onginal organic layer Removal of solvent with a rotary evaporator provides a residue (Note 8) that is transferred to a 350-mL fntted-glass funnel and tnturated successively with 200 mL and 100 mL of saturated sodium chlonde solution containing 1% sodium hydroxide (Note 9) and finally with two 50-mL portions of distilled water [Pg.86]

After ca 20 hr at 55-60°C, the mixture is cooled to room temperature using a water bath, and then 1 1 g (0 03 mol) of sodium borohydnde is [Pg.86]

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