重氮甲烷 → methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate

HRID 2370

反应方程式

HRID 2370 反应方程式
[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]

参与物

4

反应物 2

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

产物 1

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

试剂、催化剂与溶剂 1

HCID 3283乙醚溶剂

实验过程

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.

来源与证据

ORD记录
ord-5330fe2873fa4dd296b870c5f2f16b19
来源数据集
uspto-grants-1998_03
专利号
US05728866

关联笔记

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