Cyclohexanethiol → HCID 86662502, compound

HRID 445985Notes

Reaction equation

[CH2:1]([CH:5]1[CH2:11][C:10](=[O:12])[O:9][C:7](=[O:8])[CH2:6]1)[CH:2]([CH3:4])[CH3:3].[CH:13]1([SH:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>>[CH:13]1([S:19][C:10]([CH2:11][C@H:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[CH2:6][C:7]([OH:9])=[O:8])=[O:12])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Reactant 2

HCID 15290Cyclohexanethiol

HCID 11480690Dihydro-4-(2-methylpropyl)-2H-pyran-2,6(3H)-dione

Product 1

HCID 86662502HCID 86662502, compound

Procedure

A schematic of the catalytic enantioselective thiolysis of 3-isobutylglutaric anhydride using cyclohexane thiol to afford (R)-3-cyclohexylsulfanylcarbonylmethyl-5-methyl-hexanoic acid is provided in FIG. 1. Thiolysis of 3-isobutylglutaric anhydride in methyltertbutylether (MTBE), at room temperature (rt) in the presence of catalytic quantities of C1 affords 3-cyclohexylsulfanylcarbonylmethyl-5-methyl-hexanoic acid in quantitative yield with the (R) enantiomer obtained in 93% ee.

Sources & evidence

ORD record: ord-edf4098be17146188b6c8b89099af3cc
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476441B2

Reaction notes

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