3-[tert-butyl(dimethyl)silyl]oxycyclopentan-1-ol

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

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

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

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

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

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

Procedure: To a solution of 3-(tert-butyldimethylsilanyloxy)cyclopentanol (3.5 g, 16 mmol) in DCM (30 mL) was added triethylamine (2.65 mL, 19.4 mmol) and DMAP (20 mg, 0.16 mmol). The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (1.34 mL, 16.5 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was washed with water and the organic layer was dried over sodium sulfate, filtered, and concentrated. Purification of the residue by column chromatography (20% diethyl ether:hexanes) afforded 2.5 g (53%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 5.19-5.3 (m, 1H), 4.4 (m, 1H), 3.0 (s, 3H), 1.8-2.3 (m, 4H), 1.5-1.7 (m, 2H), 0.86 (s, 9H), 0.05 (s, 6H). The reaction mixture was washed with water the organic layer was dried over sodium sulfate filtered concentrated Purification of the residue by column chromatography (20% diethyl ether:hexanes)

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

Procedure: To a solution of 1,3-cyclopentanediol (5 g, 49 mmol) and imidazole (5 g, 74 mmol) in DMF (20 mL) added tert-butyldimethylsilyl chloride (5.9 g, 39 mmol). The reaction stirred for 3 h at room temperature and was then poured into water and extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (10% diethyl ether:hexanes) to afford 3.5 g (33%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 4.3-4.5 (m, 2H), 1.9-2.15 (m, 2H), 1.65-1.8 (m, 2H), 1.4-1.6 (m, 2H), 1.32-1.41 (m, 1H), 0.86 (s, 9H), 0.05 (s, 6H). extracted with diethyl ether The organic layer was washed with brine dried over sodium sulfate filtered concentrated The residue was purified by column chromatography (10% diethyl ether:hexanes)

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

Procedure: 3-(tert-Butyldimethylsilyloxy)cyclopentanol (4.8 g, 0.022 mol) and 4.22 g (0.022 mol) of tosyl chloride were mixed with 45 mL of pyridine and stinted at room temperature over night. TLC revealed the completion of the reaction. The pyridine was removed in vacuo and the residue was dissolved in ethyl acetate, washed with 1 N HCl and brine, and dried over Na2SO4. The filtrate was concentrated under vacuum to dryness to obtain 8.0 g of crude desired product as a light pink residue. The crude product was purified over SiO2 using 3% EtOAc in hexanes as eluant to give two lots material. The first lot contained 2.50 g of product approximately 90% pure. The second lot contained 2.66 g of desired product with greater than 98% purity. The combined yield was approximately 60%. stinted at room temperature over night the completion of the reaction The pyridine was removed in vacuo the residue was dissolved in ethyl acetate washed with 1 N HCl and brine dried over Na2SO4 The filtrate was concentrated under vacuum to dryness

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

Procedure: Sodium Hydride (3.77 g, 0.094 mol, 60% in mineral oil) was added to a solution of 1,3-cyclopentanediol (9.62 g, 0.094 mol) in 100 mL of THF. A slight generation of gas was observed. After stirring at room temperature for 1 h, tert-butyldimethylsilyl chloride (14.2 g, 0.094 mol) was added and the mixture was stirred at room temperature over night. The reaction mixture was diluted with 500 mL of ethylacetate and washed with 125 mL of 10% K2CO3, brine, and dried over Na2SO4. The solution was concentrated and dried in vacuo to give 20.3 g of crude product as a colorless oil. Further purification over SiO2 using a gradient elution 5% EtOAc/hexanes to 10% EtOAc/hexanes provided the desired compound as a colorless oil (7.1 g, 35% yield). the mixture was stirred at room temperature over night washed with 125 mL of 10% K2CO3, brine dried over Na2SO4 The solution was concentrated dried in vacuo to give 20.3 g of crude product as a colorless oil Further purification over SiO2 using a gradient elution 5% EtOAc/hexanes to 10% EtOAc/hexanes

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

Procedure: To a solution of 3-(tert-butyldimethylsilanyloxy)cyclopentanol (3.5 g, 16 mmol) in DCM (30 mL) was added triethylamine (2.65 mL, 19.4 mmol) and DMAP (20 mg, 0.16 mmol). The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (1.34 mL, 16.5 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was washed with water and the organic layer was dried over sodium sulfate, filtered, and concentrated. Purification of the residue by column chromatography (20% diethyl ether:hexanes) afforded 2.5 g (53%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 5.19-5.3 (m, 1H), 4.4 (m, 1H), 3.0 (s, 3H), 1.8-2.3 (m, 4H), 1.5-1.7 (m, 2H), 0.86 (s, 9H), 0.05 (s, 6H). The reaction mixture was washed with water the organic layer was dried over sodium sulfate filtered concentrated Purification of the residue by column chromatography (20% diethyl ether:hexanes)

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

Procedure: To a solution of 3-(tert-butyldimethylsilanyloxy)cyclopentanol (3.5 g, 16 mmol) in DCM (30 mL) was added triethylamine (2.65 mL, 19.4 mmol) and DMAP (20 mg, 0.16 mmol). The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (1.34 mL, 16.5 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was washed with water and the organic layer was dried over sodium sulfate, filtered, and concentrated. Purification of the residue by column chromatography (20% diethyl ether:hexanes) afforded 2.5 g (53%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 5.19-5.3 (m, 1H), 4.4 (m, 1H), 3.0 (s, 3H), 1.8-2.3 (m, 4H), 1.5-1.7 (m, 2H), 0.86 (s, 9H), 0.05 (s, 6H). The reaction mixture was washed with water the organic layer was dried over sodium sulfate filtered concentrated Purification of the residue by column chromatography (20% diethyl ether:hexanes)

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

Procedure: To a solution of 1,3-cyclopentanediol (5 g, 49 mmol) and imidazole (5 g, 74 mmol) in DMF (20 mL) added tert-butyldimethylsilyl chloride (5.9 g, 39 mmol). The reaction stirred for 3 h at room temperature and was then poured into water and extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (10% diethyl ether:hexanes) to afford 3.5 g (33%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 4.3-4.5 (m, 2H), 1.9-2.15 (m, 2H), 1.65-1.8 (m, 2H), 1.4-1.6 (m, 2H), 1.32-1.41 (m, 1H), 0.86 (s, 9H), 0.05 (s, 6H). extracted with diethyl ether The organic layer was washed with brine dried over sodium sulfate filtered concentrated The residue was purified by column chromatography (10% diethyl ether:hexanes)