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

HRID 1785720Notes

Reaction equation

HRID 1785720 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]([O:30][CH:31]([F:33])[F:32])=[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]([O:30][CH:31]([F:33])[F:32])=[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 689024852-(Trifluoromethyl)-4'-(difluoromethoxy)benzhydrolHCID 689038181-Benzhydryl-3-(2,4,4'-trichlorobenzhydryloxy)azetidine

Product 1

HCID 689036941-Benzhydryl-3-[2-(trifluoromethyl)-4'-(difluoromethoxy)-benzhydryloxy]azetidineYield 111.6%

Procedure

This material was prepared from 1-benzhydryl-3-azetidinol (1) (1.12 g, 4.7 mmol) and 2-(trifluoromethyl)-4′-(difluoromethoxy)benzhydrol (173) (3.0 g, 9.4 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 (10:90-+15:85)] to afford an amber gum (2.83 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 (10:90-+15:85)]

Sources & evidence

ORD record
ord-74ca3a7ed76e4f6a81781521e817cd43
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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