Pyridinium chloride → (+)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-(4-trifluoromethyl-phenyl)-chromen-4-one

HRID 1363355Notes

Reaction equation

[OH:1][CH2:2][C@H:3]1[C@H:7]([C:8]2[C:9]([O:31]C)=[CH:10][C:11]([O:29]C)=[C:12]3[C:17]=2[O:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:14][C:13]3=[O:28])[CH2:6][CH2:5][N:4]1[CH3:33].Cl.N1C=CC=CC=1>>[OH:29][C:11]1[CH:10]=[C:9]([OH:31])[C:8]([C@@H:7]2[CH2:6][CH2:5][N:4]([CH3:33])[C@H:3]2[CH2:2][OH:1])=[C:17]2[C:12]=1[C:13](=[O:28])[CH:14]=[C:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1)[O:16]2

Participants

Reactant 2

HCID 10176127Pyridinium chloride

HCID 66933632(+)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-(4-trifluoromethyl-phenyl)-chromen-4-one

Product 1

HCID 66933731(+)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-(4-trifluoromethyl-phenyl)-chromen-4-one

Procedure

Compound of example 64 (0.7 g, 1.51 mmol) was demethylated using pyridine hydrochloride (7 g, 60.60 mmol) as described in example 17 to obtain the title compound.

Sources & evidence

ORD record: ord-e4f19ee5eaf841a5be02ea5837097e75
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884127B2

Reaction notes

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