Farnesyl acetone → (6R,10R)-6,10,14-trimethylpentadecan-2-one

HRID 709377Notes

Reaction equation

HRID 709377 reaction equation
[CH2:1]([CH2:16][C:17](=[O:19])[CH3:18])/[CH:2]=[C:3](/[CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9])\[CH3:4].[CH3:20][C@@H:21]([CH2:28][CH2:29][CH2:30][C@@H:31]([CH3:38])[CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:22][CH2:23][CH2:24][C:25](=[O:27])[CH3:26]>>[CH3:4][C@@H:3]([CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:9])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:2][CH2:1][CH2:16][C:17](=[O:19])[CH3:18].[CH3:20][C@@H:21]([CH2:28][CH2:29][CH2:30][C@H:31]([CH3:38])[CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:22][CH2:23][CH2:24][C:25](=[O:27])[CH3:26].[CH3:4][C@H:3]([CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:9])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:2][CH2:1][CH2:16][C:17](=[O:19])[CH3:18].[CH3:4][C@H:3]([CH2:5][CH2:6][CH2:7][C@H:8]([CH3:9])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:2][CH2:1][CH2:16][C:17](=[O:19])[CH3:18]

Participants

6

Reactant 2

HCID 1711945Farnesyl acetoneHCID 1810797(6S,10S)-6,10,14-trimethylpentadecan-2-one

Product 4

HCID 1810793(6R,10R)-6,10,14-trimethylpentadecan-2-oneHCID 1810794(6R,10S)-6,10,14-trimethylpentadecan-2-oneHCID 1810796(6S,10R)-6,10,14-trimethylpentadecan-2-oneHCID 1810797(6S,10S)-6,10,14-trimethylpentadecan-2-one

Procedure

Specifically, it has been found that using the R-isomer of catalyst of formula (I) in the hydrogenation of E,E-farnesylacetone (=(5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-2-one) the hydrogenation product (6S,10S)-6,10,14-trimethylpentadecan-2-one is formed in more than 96% in respect to all of the possible stereoisomers (i.e. (6S,10S)-6,10,14-trimethylpentadecan-2-one, (6S,10R)-6,10,14-trimethylpentadecan-2-one, (6R,10S)-6,10,14-trimethylpentadecan-2-one and (6R,10R)-6,10,14-trimethylpentadecan-2-one). Hence, the corresponding (6S,10R)- and (6R,10S)- and (6R,10R)-isomers are only formed only in smaller amounts.

Sources & evidence

ORD record
ord-484ef40a30bf43fcbcd378750d863e41
Source dataset
uspto-grants-2015_11
Patent number
US09181163B2

Reaction notes

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