Phenacyl bromide → HCID 57345354, compound

HRID 1619537Notes

Reaction equation

HRID 1619537 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10]([O:12][CH:13]1[CH2:19][CH:18]2[N:20]([CH3:21])[CH:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>CN(C=O)C.C(#N)C>[Br-:28].[C:1]([O:5][C:6]([NH:8][CH:9]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:10]([O:12][CH:13]1[CH2:14][CH:15]2[N+:20]([CH3:21])([CH2:29][C:30](=[O:31])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:18]([CH2:17][CH2:16]2)[CH2:19]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 67607346HCID 67607346, compound

Product 1

HCID 57345354HCID 57345354, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (C58) (230 mg, 0.61 mmol) in DMF (15 ml) and acetonitrile (5 ml), was added 2-bromo-1-phenylethanone (134 mg, 0.68 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The crude was first triturated with i-Pr2O and then purified by flash chromatography (DCM/MeOH=94/6) to obtain 3-(2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-8-methyl-8-(2-oxo-2-phenylethyl)-8-azoniabicyclo[3.2.1]octane bromide (196 mg; 56% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was first triturated with i-Pr2O
  3. custompurified by flash chromatography (DCM/MeOH=94/6)

Sources & evidence

ORD record
ord-4dd2a91f354140149d547960ae819a43
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

Loading…