2,2,3,6-Tetramethylcyclohexanone → (-)-(3R,5R,8R)-4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane

HRID 892667Notes

Reaction equation

HRID 892667 reaction equation
[CH3:1][C:2]1([CH3:11])[CH:7]([CH3:8])[CH2:6][CH2:5][CH:4]([CH3:9])[C:3]1=[O:10].[CH3:12][C:13]1([CH3:22])[C@@H:18]([CH3:19])[CH2:17][CH2:16][C@H:15]([CH3:20])[C:14]1=[O:21].[CH3:23]C1(C)[C@H](C)CC[C@@H](C)C1=O>>[CH3:11][C:2]1([CH3:1])[C@@H:7]([CH3:8])[CH2:6][CH2:5][C@H:4]([CH3:9])[C@@:3]21[O:10][CH2:12]2.[CH3:22][C:13]1([CH3:12])[C@H:18]([CH3:19])[CH2:17][CH2:16][C@@H:15]([CH3:20])[C@:14]21[O:21][CH2:23]2

Participants

5

Reactant 3

HCID 51304442,2,3,6-TetramethylcyclohexanoneHCID 53858992(-)-(3R,6R)-2,2,3,6-tetramethyl-1-cyclohexanoneHCID 57262052(+)-(3S,6S)-2,2,3,6-tetramethyl-1-cyclohexanone

Product 2

HCID 54096983(-)-(3R,5R,8R)-4,4,5,8-tetramethyl-1-oxaspiro[2.5]octaneHCID 57201134(+)-(3S,5S,8S)-4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane

Procedure

Prepared according to the general method described, starting from 2,2,3,6-tetramethyl-1-cyclohexanone (mixture trans/cis: 85/15%) under the conditions described in published European patent application No. 0 374 509. The analytical data for this epoxide are described therein. When using as starting product (+)-(3S,6S)-2,2,3,6-tetramethyl-1-cyclohexanone ([α]20D =+52.2°) or, respectively (-)-(3R,6R)-2,2,3,6-tetramethyl-1-cyclohexanone ([α]20D =-50.7°), there were obtained the optically active isomers of the above-mentioned epoxide, i.e., (+)-(3S,5S,8S)-4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane ([α]20D =+36.0°) or, respectively (-)-(3R,5R,8R)-4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane ([α]20D =-35.1°). The analytical data of these compounds are also described in said European patent application.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-83f1817c66fb4760ad36d49ac484da9b
Source dataset
uspto-grants-1992_06
Patent number
US05118865

Reaction notes

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