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

HRID 2393905Notes

Reaction equation

HRID 2393905 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(CC)CC)C>COC(C)(C)C>[Si:1]([O:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([O:14][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54118351(1S,3R)-3-{[tert-Butyl(dimethyl)silyl]oxy}cyclopentan-1-ol

Product 1

HCID 54256983(1S,3R)-methanesulfonic acid 3-tert-butyldimethylsilyloxy-cyclopentyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
-5 °C

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) δ 5.1 (m, 1 H), 4.2 (m, 1 H), 2.99 (s, 3 H), 2.3 (m, 1 H), 2.0 (m, 3 H), 1.8 (m, 2 H), 0.88 (s, 9 H), 0.05 (s, 6 H).

Workup

  1. customthe temperature between -5° C. and -2° C.
  2. customThe ice bath is removed
  3. customThe mixture is then transferred to a separatory funnel
  4. additiontreated with brine/water (50 mL/50 mL)
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted with tert-butyl methyl ether (2×50 mL)
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2aa33df7aaa6458f97172aa6d67f5441
Source dataset
uspto-grants-1998_09
Patent number
US05808112

Reaction notes

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