Methanol → methyl (R)-3-hydroxyoctadecanoate

HRID 610782Notes

Reaction equation

HRID 610782 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:3][C:4]([O:6][CH3:7])=[O:5].CO.[H][H]>C(Cl)Cl.[Ru]>[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 887MethanolHCID 84501Methyl 3-oxooctadecanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 9858026methyl (R)-3-hydroxyoctadecanoateYield 95%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a 200-ml autoclave (made of Hastelloy) were introduced 50 g of the methyl 3-oxooctadecanoate obtained above and 50 ml of methanol. The atmosphere in the autoclave was replaced with nitrogen gas. Thereto was added a solution prepared by dissolving 325 mg of Ru2Cl4 ((+)-(T)BINAP)2Et3N as a ruthenium-optically active phosphine complex in 3.8 ml of methylene chloride. Asymmetric hydrogenation was conducted at 65° C. and a hydrogen pressure of 30 atm. After the reaction mixture was thus reacted for 12 hours, it was taken out of the autoclave. The reaction product was recrystallized from methanol to obtain 47.8 g of methyl (R)-3-hydroxyoctadecanoate. Yield, 95%.

Workup

  1. additionThereto was added a solution
  2. customprepared
  3. customwas conducted at 65° C.
  4. customAfter the reaction mixture was thus reacted for 12 hours
  5. customThe reaction product was recrystallized from methanol

Sources & evidence

ORD record
ord-313bea7b80aa4799ab6a4e0bf90ef3b2
Source dataset
uspto-grants-1999_12
Patent number
US05998668

Reaction notes

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