Toluene → rac-(2'R,3'S,4'S)-6-chloro-2'-(3-chloro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carbonyl chloride

HRID 2065403Notes

Reaction equation

HRID 2065403 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:27])[C:10]3([CH:14]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][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.C1(C)C=CC=CC=1.[C:35](Cl)([Cl:37])=[O:36].C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:27])[C:10]3([CH:14]([CH2:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:13][N:12]([C:35]([Cl:37])=[O:36])[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

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 67337897rac-(2'R,3'S,4'S)-6-chloro-2'-(3-chloro-phenyl)-4'-(2,2-dimethyl-propyl)-1H-spiro[indole-3,3'-pyrrolidin]-2-one

Product 1

HCID 76776160rac-(2'R,3'S,4'S)-6-chloro-2'-(3-chloro-phenyl)-4'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in Example 8, rac-(2′R,3′S,4′S)-6-chloro-2′-(3-chloro-phenyl)-4′-(2,2-dimethyl-propyl)-1H-spiro[indole-3,3′-pyrrolidin]-2-one prepared in Example 16 (0.3 g, 0.74 mmol) was reacted with a toluene solution (Aldrich, 20%) of phosgene (0.7 mL, 1.3 mmol) and saturated aqueous NaHCO3 solution (5 mL) in dichloromethane (5 mL) to give rac-(2′R,3′S,4′S)-6-chloro-2′-(3-chloro-phenyl)-4′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-1′-carbonyl chloride as a yellow oil (Yield, 0.34 g, 100%), which was used in the next step without further purification.

Workup

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Sources & evidence

ORD record
ord-cadddd946add4e5d9c9140c7e386568e
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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