2-pyrrolidin-1-ylcyclohexan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Cyclohexene oxide (982 mg, 10 mmol), pyrolidine (2.134 g, 30 mmol), and 1.8 mL of water were heated at 90° C. for 18 hours. The reaction was then cooled and diluted with 75 mL of diethyl ether. The mixture was then washed with aqueous sodium bicarbonate (15 mL), brine (2×15 mL), dried over magnesium sulfate, filtered, and evaporated to give 1.499 g (89%) of the title compound. The reaction was then cooled The mixture was then washed with aqueous sodium bicarbonate (15 mL), brine (2×15 mL) dried over magnesium sulfate filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of oxalyl chloride (50 mL, 0.5732 mol) in 200 mL of freshly distilled CH2Cl2 was cooled down to -70° C. and DMSO (80 mL, 1.1274 mol) was carefully added dropwise. After 15 min., 2-(1-pyrrolidinyl)cyclohexanol (a) (70 g, 0.4142 mol) was added to the reaction mixture, followed by Et3N (350 mL). The cold bath was then removed, and the mixture was stirred at room temperature for two and a half hours. Progress of the reaction was followed by gas chromatography. The solvent was partially removed in vacuo and ethyl ether (200 mL) was added. This organic layer was washed with brine (3×100 mL), dried (Na2SO4), and the solvent removed in vacuo. The crude product was distilled under high vacuum (BP: 84° C./0.5 mmHg) to yield 49.5 g of the ketone (b) as a colorless oil (72%). Rf : 0.49 (CHCl3 :MeOH:NH4OH=92:7:1); B.P: 84° C. (0.5 mmHg); IR (neat) 2940, 2860, 2800, 1715, 1440 cm-1 ; 1H-NMR (CDCl3) d 1.53-1.63 (m, 1H), 1.72 (m, 4H), 1.76-1.93 (m, 4H), 1.94-2.04 (m, 1H), 2.21, (m, 1H), 2.52 (m, 5H), 2.83 (dd, 1H, J1 =8.6, J2 =4.5 Hz); Mass Spectrum Calcd. for C10H17NO: 167.1310, Found: 167.1310. The cold bath was then removed The solvent was partially removed in vacuo and ethyl ether (200 mL) was added This organic layer was washed with brine (3×100 mL) dried (Na2SO4) the solvent removed in vacuo The crude product was distilled under high vacuum (BP: 84° C./0.5 mmHg)

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

Procedure: Cyclohexene oxide (982 mg, 10 mmol), pyrolidine (2.134 g, 30 mmol), and 1.8 mL of water were heated at 90° C. for 18 hours. The reaction was then cooled and diluted with 75 mL of diethyl ether. The mixture was then washed with aqueous sodium bicarbonate (15 mL), brine (2×15 mL), dried over magnesium sulfate, filtered, and evaporated to give 1.499 g (89%) of the title compound. The reaction was then cooled The mixture was then washed with aqueous sodium bicarbonate (15 mL), brine (2×15 mL) dried over magnesium sulfate filtered evaporated