Diazomethane → methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate

HRID 2370

Reaction equation

HRID 2370 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][C:8]([OH:10])=[O:9])[C@@H:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[N+](=[CH2:18])=[N-]>CCOCC>[OH:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][C:8]([O:10][CH3:18])=[O:9])[C@@H:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 11171909(+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid

Product 1

HCID 7075801methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

It is to be noted that (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid, used as starting product in this variant of the process of the invention, can also be directly methylated, for example by reacting it with an excess of diazomethane in ether solution, to provide pratically pure methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate, which can then be converted into (+)-cis-Hedione® via oxidation.

Sources & evidence

ORD record
ord-5330fe2873fa4dd296b870c5f2f16b19
Source dataset
uspto-grants-1998_03
Patent number
US05728866

Linked notes

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