Hydrochloric Acid → HCID 178455773, compound

HRID 1993143Notes

Reaction equation

HRID 1993143 reaction equation
[CH:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][OH:16])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)=[CH2:2].N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].Cl>CN(C)C1C=CN=CC=1.ClCCl>[CH3:23][S:24]([O:16][CH2:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([CH:1]=[CH2:2])[CH2:4][CH2:5]2)[CH2:10][CH2:11]1)(=[O:26])=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178455769HCID 178455769, compound

Product 1

HCID 178455773HCID 178455773, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

15.1 g of trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethanol, 8.2 mL of pyridine, and 0.41 g of 4-dimethylaminopyridine were dissolved in 50 mL of dichloromethane. A dichloromethane (6 mL) solution containing 6.3 mL of methanesulfonyl chloride was added dropwise to the above solution on ice for 30 minutes. The solution was heated to room temperature, then stirred for 6 hours, and was left over night. The reaction solution was poured into 10% hydrochloric acid, and the organic phase was fractioned. The water phase was extracted with dichloromethane. The organic phase was collected and washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silicagel/toluene) and recrystallization (hexane/toluene) three times, to thereby obtain 9.8 g of trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethyl methanesulfonate in the form of colorless crystals.

Workup

  1. additionwas added dropwise to the above solution on ice for 30 minutes
  2. waitwas left over night
  3. extractionThe water phase was extracted with dichloromethane
  4. customThe organic phase was collected
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by column chromatography (silicagel/toluene) and recrystallization (hexane/toluene) three times

Sources & evidence

ORD record
ord-bed5d87b51e6462e9fb93942000bbe5c
Source dataset
uspto-grants-2010_01
Patent number
US07651630B2

Reaction notes

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