Triethylamine → (1S,3R)-acetic acid 3-methanesulfonyloxy-cyclopentyl ester

Temperature

-8 °C

Dissolve (1S,3R)-cis-3-acetoxy-cyclopentanol (9.75 g, 67.6 mmol, prepared in example 23) in tert-butyl methyl ether (80 mL, anhydrous) and cool to -8° C. with stirring. Add methanesulfonyl chloride (5.7 mL, 73.6 mmol, mesyl chloride) over 5 minutes, followed by dropwise addition of triethylamine (11.4 mL, 81.2 mL), over about 30 minutes, maintaining the temperature below -2° C. The ice bath is then removed and the mixture is stirred for 2 hours. The mixture is poured into a water/brine mixture (50 mL/50 mL). The layers are separated and the aqueous layer extracted with tert-butyl methyl ether (100 mL). The organic layer and extract is combined, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (14.4 g) as a yellow oil; 1H NMR (CDCl3) δ 8 5.1 (m, 2 H), 3.02 (s, 3 H), 2.41 (m, 1 H), 2.05 (s, 3 H), 2.0 (m, 5 H).

1. temperaturemaintaining the temperature below -2° C
2. customThe ice bath is then removed
3. stirringthe mixture is stirred for 2 hours
4. additionThe mixture is poured into a water/brine mixture (50 mL/50 mL)
5. customThe layers are separated
6. extractionthe aqueous layer extracted with tert-butyl methyl ether (100 mL)
7. extractionThe organic layer and extract
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under vacuum

ORD record

ord-622e62a0bab34c45a835034991cfacd9

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05808112