HCID 10986589, compound → HCID 11829803, compound

HRID 1110164Notes

Reaction equation

HRID 1110164 reaction equation
[CH2:1]([C:8](=[O:12])[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([CH:8]([OH:12])[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 10986589HCID 10986589, compound

Product 1

HCID 11829803HCID 11829803, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

In a 500 ml stainless steel-made autoclave were charged 65.6 g (400 mmole) of 3-benzyl-3-oxopropanol and 550 mg (0.4 mmole) of [RuI(p-cymene)((R)-BINAP)]I3 synthesized in Example 1 in a nitrogen atmosphere, and 300 ml of methanol was added thereto, followed by stirring the mixture at 35° C. for 20 hours under a hydrogen pressure of 50 atm. The reaction mixture was concentrated by using rotary evaporator and then subjected to silica gel column chromatography (eluent: hexane/ethylacetate=8/2 by volume) to eliminate the complex to give 63 g of 3-benzyl-3-hydroxypropanol (96% yield). The thus obtained product was derived to the MTPA diester and subjected to high-performance liquid chromatography (column: Cosmosil-5SL, eluent: hexane/ether=8/2 by volume). As a result, it was found to have an optical purity of 97% ee.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customevaporator

Sources & evidence

ORD record
ord-36e289c7f7fd4b989b9e58309fde29d7
Source dataset
uspto-grants-1994_06
Patent number
US05324870

Reaction notes

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