Acetyl chloride → HCID 66746501, compound

HRID 471677Notes

Reaction equation

HRID 471677 reaction equation
[Cl-].[C:2]([C:4]1[C:16]([N+:17]([O-])=O)=[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:29])[CH3:28]>C1COCC1>[NH2:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:5]([O:6][CH2:7][C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:27](=[O:29])[CH3:28])[C:4]=1[C:2]#[N:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66747036HCID 66747036, compound

Product 1

HCID 66746501HCID 66746501, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (S)-2-((2-cyano-3-nitrophenoxy)methyl)pyrrolidinium chloride (130 mg, 0.46 mmol) (Example 209b) in THF (5 mL) were added Et3N (135 μL, 0.97 mmol) and acetyl chloride (36 μL, 0.50 mmol). The reaction was stirred at rt for 18 h, filtered and diluted with EtOH (20 mL). The resulting solution was hydrogenated (20 Bar) using 10% Pd/C as the catalyst. Upon completion, the reaction mixture was concentrated to provide the title compound (61 mg, 51%) as a clear syrup. MS 260 (MH+).

Workup

  1. filtrationfiltered
  2. additiondiluted with EtOH (20 mL)
  3. concentrationUpon completion, the reaction mixture was concentrated

Sources & evidence

ORD record
ord-728c1e9cb13e44de9de3d5e7b6db5ad9
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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