Acetyl chloride → HCID 66746501, compound

HRID 711815Notes

Reaction equation

HRID 711815 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-50ab63353ba9436abff9a7240d73df53
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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