tert-Butyl chloroacetate → HCID 70673630, compound

HRID 1910501Notes

Reaction equation

HRID 1910501 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([O:11][CH:12]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:10])[CH2:2]2.[Cl:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C(#N)C>[Cl-:27].[F:26][C:22]1[CH:21]=[C:20]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[O:11][C:9]([CH:3]2[CH:4]3[CH2:5][CH2:6][N+:1]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([CH2:8][CH2:7]3)[CH2:2]2)=[O:10])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 66052tert-Butyl chloroacetate2×HCID 70925896Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate

Product 1

HCID 70673630HCID 70673630, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate (70 mg, 0.20 mmol, prepared as in example 4) and tert-butyl 2-chloroacetate (31 μl, 0.21 mmol) were dissolved in acetonitrile (3 ml) and stirred at room temperature overnight. Tert-butyl 2-chloroacetate (28 μl, 0.20 mmol) was added again, and the mixture was stirred for additional 24 hours. Acetonitrile was evaporated, and the resulting crude compound was triturated from Et2O and filtered to obtain 3-((bis(3-fluorophenyl)methoxy)carbonyl)-1-(2-tert-butoxy-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane chloride (42.4 mg, racemic mixture).

Workup

  1. stirringthe mixture was stirred for additional 24 hours
  2. customAcetonitrile was evaporated
  3. customthe resulting crude compound was triturated from Et2O
  4. filtrationfiltered

Sources & evidence

ORD record
ord-3d9eb796f2da440c93358be503ab396d
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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