Formic Acid → HCID 59203391, compound

HRID 1173776Notes

Reaction equation

HRID 1173776 reaction equation
[Cl:1][CH:2]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.C(O)=O>CN(C=O)C>[Cl:1][C@@H:2]([C@H:8]([OH:12])[CH2:9][CH2:10][CH3:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 11424094Ethyl 2-chloro-3-oxohexanoate

Product 1

HCID 59203391HCID 59203391, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-chloro-3-oxohexanoate (194 mg), DMF (2.4 ml), RuCl[(S,S)-MesDPEN](p-cymene) complex (1 mol %) and triethylamine (5 equivalents) were mixed, and formic acid (5 equivalents) was gradually added thereto. The reaction was carried out at 40° C. for 3 hours. The reaction mixture was analyzed. As a result, the conversion ratio was 97%, and the isomer ratio of (2S,3R):(2S,3S):(2R,3R):(2R,3S) is 94.7:1.3:0:4.0. In the above, “Mes” represents a methylenesulfonyl group.

Sources & evidence

ORD record
ord-4e6f2b96e1574700a0e970ea4c39617e
Source dataset
uspto-grants-2010_11
Patent number
US07834190B2

Reaction notes

Loading…