Diethyl Ether → HCID 86688879, compound

HRID 404618Notes

Reaction equation

HRID 404618 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)=[O:4].[C:10]1([CH:16]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:17]([O:19][C@@H:20]2[CH:25]3[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]3)[CH2:21]2)=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCOCC>C(OCC)(=O)C.C(#N)C>[Br-:1].[O:4]=[C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)[CH2:2][N+:22]12[CH2:23][CH2:24][CH:25]([CH2:26][CH2:27]1)[C@@H:20]([O:19][C:17](=[O:18])[CH:16]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)[CH2:21]2

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneHCID 71603247(R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate

Product 1

HCID 86688879HCID 86688879, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(thiophen-3-yl)ethanone (54.9 mg, 0.27 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (80 mg, 0.24 mmol) in ethyl acetate (1.2 ml) and acetonitrile (1.2 ml). The reaction was stirred at room temperature for 24 h (UPLC-MS: complete conversion). The solvents were evaporated and the residue was purified first by flash chromatography (DCM/MeOH=92/8) and then by trituration with Et2O to obtain compound (3R)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-3-(2-phenyl-2-(piperidin-1-yl)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (96 mg, 73.9% yield) as a white solid.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified first by flash chromatography (DCM/MeOH=92/8)

Sources & evidence

ORD record
ord-cf90a3692d5c4fd29e32300d7d856fe9
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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