m-Chloroperbenzoic acid → 4-[7-Chloro-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinoline-6-sulfinyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 404755Notes

Reaction equation

HRID 404755 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[Cl:25])[C:21](=[O:26])[N:20]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:44])C=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([S:14]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[Cl:25])[C:21](=[O:26])[N:20]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[CH:19]=[CH:18]3)=[O:44])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 592906794-[7-Chloro-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-ylsulfanyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 685931954-[7-Chloro-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinoline-6-sulfinyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

206 mg 4-[7-Chloro-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-ylsulfanyl]-piperidine-1-carboxylic acid tert-butyl ester (285) in 6 ml of dichloromethane were treated with 83 mg m-Chloroperbenzoic acid over 2 h. The mixture was diluted with dichloromethane and washed with sodium hydrogen carbonate solution and brine. After drying over sodium sulfate all volatiles were evaporated and the crude product purified by chromatography 2:1 (ethyl acetate/Heptane) to obtain 4-[7-Chloro-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinoline-6-sulfinyl]-piperidine-1-carboxylic acid tert-butyl ester as an off white solid.

Workup

  1. washwashed with sodium hydrogen carbonate solution and brine
  2. dry with materialAfter drying over sodium sulfate all volatiles
  3. customwere evaporated
  4. customthe crude product purified by chromatography 2:1 (ethyl acetate/Heptane)

Sources & evidence

ORD record
ord-c4974ae59947483f8ef35a70c68df935
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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