tert-Butyl bromoacetate → HCID 86665820, compound

HRID 1619507Notes

Reaction equation

HRID 1619507 reaction equation
[Br:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:10]([O:14][C:15]([NH:17][CH:18]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:19]([O:21][C@@H:22]1[CH:27]2[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]2)[CH2:23]1)=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(#N)C>[Br-:1].[C:6]([O:5][C:3](=[O:4])[CH2:2][N+:24]12[CH2:25][CH2:26][CH:27]([CH2:28][CH2:29]1)[C@@H:22]([O:21][C:19](=[O:20])[CH:18]([NH:17][C:15]([O:14][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:16])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:23]2)([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 67425060(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate

Product 1

HCID 86665820HCID 86665820, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tert-butyl 2-bromoacetate (29.5 μl, 0.20 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (C1) (72 mg, 0.20 mmol) in acetonitrile (3 ml). The reaction was stirred at RT overnight. The product was collected by suction filtration and then purified by flash chromatography (DCM/MeOH=98/2 to 95/5) to get (3R)-1-(2-tert-butoxy-2-oxoethyl)-3-(2-(tert-butoxycarbonylamino)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane bromide (97 mg; 87% yield).

Workup

  1. filtrationThe product was collected by suction filtration
  2. custompurified by flash chromatography (DCM/MeOH=98/2 to 95/5)

Sources & evidence

ORD record
ord-4c09199d20f844f0af240eebb3003a22
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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