Dichloromethane → 3-(4-Chlorophenyl)-3-{7-[(methylsulfinyl)methyl]-1H-indol-3-yl}pentan-1-ol

HRID 561611Notes

Reaction equation

HRID 561611 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:14]2[C:22]3[C:17](=[C:18]([CH2:23][S:24][CH3:25])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)([CH2:12][CH3:13])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:37])C=1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:14]2[C:22]3[C:17](=[C:18]([CH2:23][S:24]([CH3:25])=[O:37])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)([CH2:12][CH3:13])[CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 583924873-(4-Chlorophenyl)-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}pentan-1-ol

Product 1

HCID 445953863-(4-Chlorophenyl)-3-{7-[(methylsulfinyl)methyl]-1H-indol-3-yl}pentan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

60 mg (0.16 mmol) of the compound from Example 140 were introduced into 6 ml of dichloromethane at 0° C., 40 mg (0.16 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT for 2 h. 2 ml of methanol were added, and the solution was concentrated. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 62 mg (99% of theory) of the title compound as mixture of diastereomers.

Workup

  1. concentrationthe solution was concentrated
  2. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-f23eb96edf554fb78abee58aa92deff7
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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