Dichloromethane → HCID 66662126, compound

HRID 557943Notes

Reaction equation

HRID 557943 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH2:16][C@@H:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:35])C=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH2:16][C@@H:15]([C:18]4[CH:23]=[CH:22][N+:21]([O-:35])=[CH:20][CH:19]=4)[CH2:14]3)=[O:12])[CH2:9][CH2:10]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 66661760HCID 66661760, compound

Product 1

HCID 66662126HCID 66662126, compound

Conditions

Temperature
25 °C

Procedure

4-((3S)-1-{[1-(4-Chlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-yl)pyridine (20 mg, 0.00006 mol, example 24) was dissolved in dichloromethane (1 mL, 0.02 mol) and to this solution was added m-chloroperbenzoic acid (44 mg, 0.00015 mol). The reaction mixture was stirred at 25° C. for 2.5 h. The reaction mixture then was concentrated and the residue was diluted with NaHCO3 and methanol. The crude product was purified by prep-HPLC. LCMS: m/z 343.4 (M+H)+.

Workup

  1. concentrationThe reaction mixture then was concentrated
  2. additionthe residue was diluted with NaHCO3 and methanol
  3. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-2c483df08b6f40f684eb945f909f5ebe
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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