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Phenacyl bromide → HCID 86665836, compound

HRID 1619527
Notes
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Reaction equation

HRID 1619527 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]([O:15][C:16]([NH:18][CH:19]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:20]([O:22][C@@H:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1)=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]>CCOC(C)=O.C(#N)C>[O:4]([CH:3]([CH3:2])[CH3:5])[CH:11]([CH3:13])[CH3:12].[Br-:1].[C:11]([O:15][C:16]([NH:18][CH:19]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:20]([O:22][C@@H:23]1[CH:28]2[CH2:27][CH2:26][N+:25]([CH2:2][C:3](=[O:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)([CH2:30][CH2:29]2)[CH2:24]1)=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6259Phenacyl bromideHCID 67606948HCID 67606948, compound

Product 2

HCID 7914Diisopropyl EtherHCID 86665836HCID 86665836, compoundYield 114.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

2-Bromo-1-phenylethanone (39.3 mg, 0.20 mmol) is added to a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(4-methoxyphenyl)acetate (C44) (70.0 mg, 0.18 mmol) in EtOAc (2 ml) and acetonitrile (2 ml). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated and the resulting colorless oil was triturated first with i-Pr2O/EtOAc (10/1) and then with i-Pr2O to obtain (3R)-3-(2-(tert-butoxycarbonylamino)-2-(4-methoxyphenyl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (60.9 mg; 58% yield).

Workup

  1. customthe solvent was evaporated
  2. customthe resulting colorless oil was triturated first with i-Pr2O/EtOAc (10/1)

Sources & evidence

ORD record
ord-43c63f99130242daba95f61355d7a03e
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772314B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes