Methanol → HCID 57062068, compound

HRID 2289387Notes

Reaction equation

HRID 2289387 reaction equation
CO.[CH3:3][C@H:4]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:5][C:6](=[O:15])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>C(Cl)Cl>[OH:15][C@@H:6]([CH2:5][C@H:4]([CH3:3])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

4

Reactant 2

HCID 887MethanolHCID 53727906HCID 53727906, compound

Product 1

HCID 57062068HCID 57062068, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 200 ml autoclave were charged 50 ml of methanol, 14.0 g of t-butyl (R)-5-methyl-3-oxononanoate obtained in Step 5, and a solution of 0.49 g of (S)-di[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]tetrachlorodiruthenium triethylamine in 40 ml of methylene chloride, and the mixture was allowed to react under a hydrogen pressure of 60 kg/cm2 for 18 hours. The solvent was removed by distillation under reduced pressure to obtain 13.6 g of a crude product, which was then purified by silica gel column chromatography to obtain 10.3 g (72.5%) of the titled compound.

Workup

  1. customto react under a hydrogen pressure of 60 kg/cm2 for 18 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customto obtain 13.6 g of a crude product, which
  4. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-151283faef6f49fc835b8bc8253a4238
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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