HCID 86590216, compound → HCID 22486359, compound

HRID 2181398Notes

Reaction equation

HRID 2181398 reaction equation
[C:1]([C:3](=[CH:9][CH:10]([CH3:12])[CH3:11])[CH2:4][C:5]([O:7][CH3:8])=[O:6])#[N:2].[H][H]>CO>[C:1]([CH:3]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:4][C:5]([O:7][CH3:8])=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 86590216HCID 86590216, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22486359HCID 22486359, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By following the general procedure of Example 3.1, 200 mg (1.190 mmol) of methyl 3-cyano-5-methyl-hex-3-enoate was dissolved in 3 mL of methanol and reacted with hydrogen gas (60 psi) in the presence of 43 mg (0.06 mmol) of [(R,R)-Et-DuPHOS]Rh(COD)+BF4− to afford 10% conversion to methyl 3-cyano-5-methylhexanoate having 33% e.e. (R).

Sources & evidence

ORD record
ord-2ff6584886fc46b39cb3f8dadacc01ce
Source dataset
uspto-grants-2005_05
Patent number
US06891059B2

Reaction notes

Loading…