3-(2,4,4'-Trichlorobenzhydryloxy)azetidine → 3-[2-(Trifluoromethyl)-4'-(methylsulfonyl)benzhydryloxy]azetidine

HRID 1785717Notes

Reaction equation

HRID 1785717 reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][CH:19]([C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC1C=C(Cl)C=CC=1C(OC1CNC1)C1C=CC(Cl)=CC=1>>[F:29][C:26]([F:27])([F:28])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:19]([O:18][CH:16]1[CH2:17][NH:14][CH2:15]1)[C:30]1[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 689025303-(2,4,4'-Trichlorobenzhydryloxy)azetidineHCID 689025351-Benzhydryl-3-[2-(trifluoromethyl)-4'-(methylsulfonyl)benzhydryloxy]azetidine

Product 1

HCID 689037193-[2-(Trifluoromethyl)-4'-(methylsulfonyl)benzhydryloxy]azetidineYield 9%

Procedure

This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4′-(methylsulfonyl)benzhydryloxy]azetidine (170) (6.9 mmol) using the procedure described for compound (4). After basic aqueous workup, purification by flash column chromatography [SiO2; ethyl acetate-methanol (90:10)→ethyl acetate-methanol—ammonium hydroxide (90:10:5)] afforded the desired product as a pale yellow oil (234 mg, 9% over 2 steps).

Workup

  1. customAfter basic aqueous workup, purification by flash column chromatography [SiO2; ethyl acetate-methanol (90:10)→ethyl acetate-methanol—ammonium hydroxide (90:10:5)]

Sources & evidence

ORD record
ord-60b0a6d711754491a673488e4c8ca64b
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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