Lawesson's reagent → racemic (2'S,3R)-6-chloro-2'-(3-chlorophenyl)-4'-isopropyl-6'-thioxospiro[3H-indole-3,3'-piperidine]-2(1H)-one

HRID 1727993Notes

Reaction equation

HRID 1727993 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:27])[C:10]3([CH:15]([CH:16]([CH3:18])[CH3:17])[CH2:14][C:13](=O)[NH:12][CH:11]3[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:5]2=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:37]2)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:27])[C:10]3([CH:15]([CH:16]([CH3:18])[CH3:17])[CH2:14][C:13](=[S:37])[NH:12][CH:11]3[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 1317273056-chloro-2'-(3-chlorophenyl)-4'-isopropyl spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 131727321racemic (2'S,3R)-6-chloro-2'-(3-chlorophenyl)-4'-isopropyl-6'-thioxospiro[3H-indole-3,3'-piperidine]-2(1H)-oneYield 95.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of racemic (2′S,3R)-6-chloro-2′-(3-chlorophenyl)-4′,4′-isopropylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (60 mg, 0.15 mmol) prepared in example 3b and 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (100 mg, 0.25 mmol) (Aldrich) in toluene (20 mL) was heated at 120° C. for 0.5 h. The mixture was cooled to room temperature and then concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:1) to give racemic (2′S,3R)-6-chloro-2′-(3-chlorophenyl)-4′-isopropyl-6′-thioxospiro[3H-indole-3,3′-piperidine]-2(1H)-one as a white solid (Yield 60 mg, 92%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography (EtOAc:hexanes=1:1)

Sources & evidence

ORD record
ord-2eec406490154f83b521b5f1bcff54ae
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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