1-Indanone → (R)-(-)-1-Indanol

HRID 1505747Notes

Reaction equation

HRID 1505747 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H][H]>CO>[C@H:1]1([OH:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 67351-IndanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 6971243(R)-(-)-1-Indanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In a 50-ml autoclave, 3.3 mg (0.005 mmol, S/C=1000) of RuCl(R,R)—O-HT-Tsdpen) was placed, and the autoclave was purged with nitrogen. Subsequently, 0.66 g (5.0 mmol) of 1-indanone and 4.4 ml of methanol were added thereto, then hydrogen gas was charged to 3.0 MPa. Subsequently, the mixture was stirred for 20 hours at 60° C. The reaction liquid was subjected to a GC analysis, and as a result, (R)-1-indanol was obtained at a conversion rate of 58.6% with an optical purity of 97.8% ee.

Workup

  1. customthe autoclave was purged with nitrogen
  2. customThe reaction liquid

Sources & evidence

ORD record
ord-f49e843c0f9441d4a502a6d4a73641b3
Source dataset
uspto-grants-2015_12
Patent number
US09217005B2

Reaction notes

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