1-(Diphenylmethyl)azetidin-3-ol → 1-Benzhydryl-3-[2-(trifluoromethyl)-4'-(methylsulfonyl)benzhydryloxy]azetidine

HRID 1785716Notes

Reaction equation

HRID 1785716 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][C:20]([F:40])([F:39])[C:21]1[CH:38]=[CH:37][CH:36]=[CH:35][C:22]=1[CH:23](O)[C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1.C(N1CC(OC(C2C=CC(Cl)=CC=2)C2C=CC(Cl)=CC=2Cl)C1)(C1C=CC=CC=1)C1C=CC=CC=1>>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][CH:23]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[C:22]2[CH:35]=[CH:36][CH:37]=[CH:38][C:21]=2[C:20]([F:19])([F:39])[F:40])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 689024622-(Trifluoromethyl)-4'-(methylsulfonyl)benzhydrolHCID 689038181-Benzhydryl-3-(2,4,4'-trichlorobenzhydryloxy)azetidine

Product 1

HCID 689025351-Benzhydryl-3-[2-(trifluoromethyl)-4'-(methylsulfonyl)benzhydryloxy]azetidineYield 44.4%

Procedure

This material was prepared from 1-benzhydryl-3-azetidinol (1) (6.9 mmol) and 2-(trifluoromethyl)-4′-(methylsulfonyl)benzhydrol (169) (13.8 mmol) using the procedure described for compound (3). After basic aqueous workup, the crude product was partially purified by flash column chromatography [SiO2; ethyl acetate-iso-hexane (30:70→80:20)] to afford an off-white foam (1.69 g) which was used directly in the next step without further purification.

Workup

  1. customAfter basic aqueous workup, the crude product was partially purified by flash column chromatography [SiO2; ethyl acetate-iso-hexane (30:70→80:20)]

Sources & evidence

ORD record
ord-634ac4484cfe4f599103e9afa830d46a
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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