(1,4-Dioxaspiro(4.5)decan-2-yl)methanol → 2-(((4-((2s)-1,4-Dioxaspiro[4.5]dec-2-ylmethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HRID 31691Notes

Reaction equation

[Na:1].C(C1(C[CH2:15][O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([CH2:23][S:24]([C:26]3[NH:30][C:29]4[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=4[N:27]=3)=[O:25])[C:18]=2[CH3:35])OCC2(OCCO2)CO1)C.ClC1C=CC=C(C(OO)=O)C=1.[O:47]1[C:51]2([CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)[O:50][CH2:49][CH:48]1CO>>[Na:1].[O:47]1[C:51]2([CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)[O:50][CH2:49][C@@H:48]1[CH2:15][O:16][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([CH2:23][S:24]([C:26]2[NH:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[N:30]=2)=[O:25])[C:18]=1[CH3:35]

Participants

Reactant 3

HCID 20128(1,4-Dioxaspiro(4.5)decan-2-yl)methanol

HCID 70297m-Chloroperbenzoic acid

HCID 667761962-(((4-(2-(8-Ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

Product 1

HCID 667765772-(((4-((2s)-1,4-Dioxaspiro[4.5]dec-2-ylmethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium saltYield 16.8%

Procedure

The same procedure as in the steps (4f) to (4j) of Example 4 (a reprecipitation operation was not performed in oxidation step with 3-chloroperbenzoic acid) was repeated using (+)-1,4-dioxaspiro[4.5]decane-2-methanol to obtain the title compound (500 mg, total 16.8% yield) as a white solid.

Sources & evidence

ORD record: ord-ee29ebc8d72241f6a1ef6e2c8152d012
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425634B2

Reaction notes

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