Allyl chloride → HCID 53906958, compound

HRID 2260613Notes

Reaction equation

[Si]([O:8][C@:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22][C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]4)[CH:17]=2)[CH2:14][CH2:13][O:12][C@@H:11]([CH3:15])[CH2:10]1)(C(C)(C)C)(C)C.[CH2:34](Cl)[CH:35]=[CH2:36].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH2:36]([N:29]1[C:30]2[C:25](=[CH:24][C:23]([S:22][C:18]3[CH:17]=[C:16]([C@@:9]4([OH:8])[CH2:14][CH2:13][O:12][C@@H:11]([CH3:15])[CH2:10]4)[CH:21]=[CH:20][CH:19]=3)=[CH:32][CH:31]=2)[CH2:26][CH2:27][C:28]1=[O:33])[CH:35]=[CH2:34]

Participants

Reactant 3

HCID 7850Allyl chloride

HCID 2724141Tetrabutylammonium Fluoride

HCID 53833969HCID 53833969, compound

Product 1

HCID 53906958HCID 53906958, compoundYield 86%

Procedure

Using an analogous procedure to that described in Example 18, (2S,4R)-4-(tert-butyldimethylsilyloxy)-2-methyl-4-[3-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]tetrahydropyran was reacted with allyl chloride and the resultant product was treated with tetrabutylammonium fluoride to give (2S,4R)-4-[3-(1-allyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylthio)phenyl]-4-hydroxy-2-methyltetrahydropyran in 86% yield, m.p. 107°-109° C. (recrystallised from diethyl ether);

Sources & evidence

ORD record: ord-30a45755a97548758920ebef63db6fd5
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05478842

Reaction notes

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