18-Crown-6 → (S)-5-Bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 1505039Notes

Reaction equation

HRID 1505039 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:12][C@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1)[CH2:7]2.[O-:20][Mn](=O)(=O)=O.[K+].C1OCCOCCOCCOCCOCCOC1>ClCCl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:12][C@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1)[C:7]2=[O:20]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 516875Potassium PermanganateHCID 58317930(S)-5-Bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 58317912(S)-5-Bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture containing (S)-5-bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1,2,3,4-tetrahydroisoquinoline (303 mg, 0.93 mmol), KMnO4 (176 mg, 1.12 mmol), 18-crown-6 (2-(5 mg, 0.93 mmol) in dichloromethane (4 ml) is stirred at room temperature for 18 hours. The reaction mixture is filtered through a celite pad and the filtrate is concentrated to dryness by rotary evaporation to give (S)-5-Bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one (LC-MS m/z: 341.2 (M+1)), which is used without further purification in the next step.

Workup

  1. filtrationThe reaction mixture is filtered through a celite pad
  2. concentrationthe filtrate is concentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-626529c931d146358509eaa041f15e76
Source dataset
uspto-grants-2015_12
Patent number
US09216964B2

Reaction notes

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