Triethylamine → HCID 66745725, compound

HRID 471642Notes

Reaction equation

HRID 471642 reaction equation
[Cl-].[C:2]([C:4]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][CH2:7][C@H:8]1[CH2:12][CH2:11][CH2:10][NH2+:9]1)#[N:3].CCN(CC)CC.[C:27](Cl)(=[O:31])[CH2:28][CH2:29][CH3:30]>C1COCC1>[C:27]([N:9]1[CH2:10][CH2:11][CH2:12][C@@H:8]1[CH2:7][O:6][C:5]1[CH:13]=[CH:14][CH:15]=[C:16]([N+:17]([O-:19])=[O:18])[C:4]=1[C:2]#[N:3])(=[O:31])[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 66746622HCID 66746622, compound

Product 1

HCID 66745725HCID 66745725, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (R)-2-((2-cyano-3-nitrophenoxy)methyl)pyrrolidinium chloride (140 mg, 0.49 mmol) (Example 176c) in THF (3 mL) were added Et3N (143 μL, 1.03 mmol) and butyryl chloride (56 μL, 0.54 mmol). The reaction was stirred for 72 h at rt under N2. Upon completion, the reaction was filtered, and the filtrate was concentrated to provide (R)-2-((1-butyrylpyrrolidin-2-yl)methoxy)-6-nitrobenzonitrile (127 mg, 82%) as a yellow syrup. MS 318 (MH+).

Workup

  1. filtrationUpon completion, the reaction was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c9fcbea7c67d483e9c854f8557579046
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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