Hydrochloric Acid → 4-{[tert-Butyl(dimethyl)silyl]oxy}-3-fluorocyclohexyl methanesulfonate

HRID 1970987Notes

Reaction equation

HRID 1970987 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH:10]1[F:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(=O)(O)[O-].[Na+].Cl>C(Cl)Cl>[CH3:17][S:18]([O:15][CH:12]1[CH2:13][CH2:14][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:10]([F:16])[CH2:11]1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 595431354-{[Tert-butyl(dimethyl)silyl]oxy}-3-fluorocyclohexanol

Product 1

HCID 595431564-{[tert-Butyl(dimethyl)silyl]oxy}-3-fluorocyclohexyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-{[tert-butyl(dimethyl)silyl]oxy}-3-fluorocyclohexanol (500 mg, 2.01 mmol) and TEA (0.56 mL, 4.03 mmol) in DCM (5 mL) was added MsCl (0.28 mL, 3.6 mmol) at 0° C. The reaction mixture was warmed to room temperature, left to stir for 1 h, treated with sodium bicarbonate solution, and neutralized with 1 N HCl. The mixture was extracted with DCM. The combined organics were dried, and concentrated to afford the title compound.

Workup

  1. waitleft
  2. extractionThe mixture was extracted with DCM
  3. customThe combined organics were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e2145f3596e943008256e96fcebd68c3
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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