4-Toluenesulfonyl chloride → HCID 86612270, compound

HRID 2355197Notes

Reaction equation

HRID 2355197 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>>[S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)([OH:1])(=[O:13])=[O:12].[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 136319Chroman

Product 1

HCID 86612270HCID 86612270, compound

Procedure

In step 8, a ring closure is effected by treatment of diol s with palladium diacetate in the presence of 2[P(t-Bu)2]-1,1-binaphthyl, to afford chroman compound t. Chroman t is treated with tosyl chloride to form chroman tosylate u in step 9. In step 10, tosylate u is reacted with amine v to afford chroman w, which is a compound of formula I in accordance with the invention.

Sources & evidence

ORD record
ord-6738a4fc37004a38b39158323ab8d546
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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