Triethylamine → 1-Adamantylmethyl methanesulfonate

HRID 605577Notes

Reaction equation

HRID 605577 reaction equation
[C:1]12([CH2:11][OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:20][S:21]([O:12][CH2:11][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol

Product 1

HCID 28017761-Adamantylmethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3 g of adamantan-1-ylmethanol and 5 ml of triethylamine in 50 ml of DCM is cooled to 0° C., 2 ml of methanesulfonyl chloride are added dropwise, and the mixture is left to stir while allowing the temperature to return to AT. A mixture of water/ice is added to the reaction mixture, the mixture is extracted with DCM, the organic phase is dried over Na2SO4, and the solvent is evaporated off under vacuum. 2 g of the expected compound are obtained.

Workup

  1. waitthe mixture is left
  2. additionis added to the reaction mixture
  3. extractionthe mixture is extracted with DCM
  4. dry with materialthe organic phase is dried over Na2SO4
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-27c6b6321323431a8af077abd2c5bb7f
Source dataset
uspto-grants-2011_03
Patent number
US07915258B2

Reaction notes

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