Diisopropylethylamine → 2-(4-Bromo-phenyl)-1-[3-(tert-butyl-diphenyl-silanyloxy)-azetidin-1-yl]-ethanone

HRID 717104Notes

Reaction equation

HRID 717104 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[C:12]([Si:16]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[O:17][CH:18]1[CH2:21][NH:20][CH2:19]1)([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:20]2[CH2:19][CH:18]([O:17][Si:16]([C:12]([CH3:15])([CH3:14])[CH3:13])([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 178425313-((Tert-butyldiphenylsilyl)oxy)azetidine

Product 1

HCID 1232758882-(4-Bromo-phenyl)-1-[3-(tert-butyl-diphenyl-silanyloxy)-azetidin-1-yl]-ethanoneYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-bromophenyl acetylchloride (300 mg, 1.28 mmol) in CH2Cl2 (5 mL) was added 3-(tert-Butyl-diphenyl-silanyloxy)-azetidine (399 mg, 1.28 mmol), DIPEA (670 μL, 3.85 mmol) and the reaction stirred at RT for 2 h. The crude material was purified by silica gel column chromatography, eluting with isohexane and increasing the polarity to 80% EtOAc/isohexane to obtain 2-(4-bromo-phenyl)-1-[3-(tert-butyl-diphenyl-silanyloxy)-azetidin-1-yl]-ethanone as a colourless glass (632 mg, 97%).

Workup

  1. customThe crude material was purified by silica gel column chromatography
  2. washeluting with isohexane
  3. temperatureincreasing the polarity to 80% EtOAc/isohexane

Sources & evidence

ORD record
ord-f10496efb9dc474ca8b5ef27f174cf2b
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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