Reaction #2658

Reaction equation

(-)-cis-3-tert-butyldimethylsilyloxy-cyclopentanol

methanesulfonyl chloride

triethylamine

→

title compound

Yield 97.0%

(1S,3R)-methanesulfonic acid 3-tert-butyldimethylsilyloxy-cyclopentyl ester

Yield 97.0%

Solvents

tert-butyl methyl ether

Conditions

Workup

1. 1
   Otherthe temperature between -5° C. and -2° C.
2. 2
   OtherThe ice bath is removed
3. 3
   OtherThe mixture is then transferred to a separatory funnel
4. 4
   workup.ADDITIONtreated with brine/water (50 mL/50 mL)
5. 5
   OtherThe layers are separated
6. 6
   Extractionthe aqueous layer is extracted with tert-butyl methyl ether (2×50 mL)
7. 7
   Washwashed with brine
8. 8
   Dryingdried over anhydrous magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated under vacuum

Procedure

Dissolve (-)-cis-3-tert-butyldimethylsilyloxy-cyclopentanol (9.20 g, 42.5 mmol) in anhydrous tert-butyl methyl ether (50 mL) and cool to -5° C. Treat the solution with methanesulfonyl chloride (3.6 g, 46.5 mmol, mesyl chloride), followed by triethylamine (7.2 mL, 51.7 mmol), at such a rate as to keep the temperature between -5° C. and -2° C. with an ice bath. The ice bath is removed and the solution is stirred for 2 hours. The mixture is then transferred to a separatory funnel and treated with brine/water (50 mL/50 mL). The layers are separated and the aqueous layer is extracted with tert-butyl methyl ether (2×50 mL). The organic layer and extracts are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (12.1 g, 97% yield) as a colorless oil; 1 H NMR (CDCl3) δ5.1 (m, 1H), 4.2 (m, 1H), 2.99 (s, 3H), 2.3 (m, 1H), 2.0 (m, 3H), 1.8 (m, 2H), 0.88 (s, 9H), 0.05 (s, 6H).

Source