2,2-Dimethoxypropane → HCID 86588954, compound

HRID 900495Notes

Reaction equation

HRID 900495 reaction equation
O[CH2:2][CH2:3][C@H:4](O)[C:5]([CH3:9])([CH3:8])[C:6]#[N:7].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[CH3:26][O:27][C:28]([O:31][CH3:32])([CH3:30])[CH3:29]>>[CH3:26][O:27][C:28]([O:31][CH3:32])([CH3:30])[CH3:29].[CH3:8][C:5]([CH3:9])([CH2:4][CH2:3][CH3:2])[C:6]#[N:7]

Participants

4

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 9833987HCID 9833987, compound2×

Product 1

HCID 86588954HCID 86588954, compound

Procedure

6.73 g (47 mmol) of 5-hydroxy-2,2-dimethyl-3(S)-hydroxy-pentane-nitrile of the title compound of Example 1d is dissolved in 27 ml of acetone dimethylketal, and 546 mg of camphor-10-sulfonic acid is added. It is heated for 15 hours to 50° C. It is evaporated to the dry state in a vacuum. The residue is taken up in 200 ml of methylene chloride and washed with saturated sodium bicarbonate solution and then with saturated sodium chloride solution. The organic phase is dried on sodium sulfate and evaporated to the dry state in a vacuum. The oil that is obtained crystallizes while standing.

Workup

  1. temperatureIt is heated for 15 hours to 50° C
  2. customIt is evaporated to the dry state in a vacuum
  3. washwashed with saturated sodium bicarbonate solution
  4. customThe organic phase is dried on sodium sulfate
  5. customevaporated to the dry state in a vacuum
  6. customThe oil that is obtained
  7. customcrystallizes

Sources & evidence

ORD record
ord-c4202dc56e9c4fbe94dfb4220b7179da
Source dataset
uspto-grants-2008_04
Patent number
US07358382B2

Reaction notes

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