Réaction #1019128

Équation de réaction

(rac) (2′S,3′R,5′S)-5′-allyl-6-chloro-3′-(3-chlorophenyl)-1′-(cyclopropylmethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)spiro[indoline-3,2′-piperidine]-2,6′-dione

sodium periodate

H2O CCl4 MeCN

citric acid

→

title compound

(rac) 2-((2′S,3′R,5′R)-6-chloro-3′-(3-chlorophenyl)-1′-(cyclopropylmethyl)-2,6′-dioxo-1-((2-(trimethylsilyl)ethoxy)methyl)spiro[indoline-3,2′-piperidine]-5′-yl)acetic acid

Conditions de réaction

Traitement

1. 1
   Filtrationfiltered through a plug of celite
2. 2
   Lavagewashed with EtOAc
3. 3
   AutreThe filtrate was transferred to a separatory funnel
4. 4
   Extractionextracted with EtOAc
5. 5
   SéchageThe organic layer was dried over Na2SO4
6. 6
   Concentrationconcentrated under reduced pressure

Mode opératoire

To a rapidly stirred solution of (rac) (2′S,3′R,5′S)-5′-allyl-6-chloro-3′-(3-chlorophenyl)-1′-(cyclopropylmethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)spiro[indoline-3,2′-piperidine]-2,6′-dione (Example 62, Step J) (46 mg, 0.079 mmol) in H2O/CCl4/MeCN (0.75 ml/0.5 mL/0.5 mL) was added sodium periodate (67.2 mg, 0.314 mmol) and ruthenium(III) chloride hydrate (1.771 mg, 7.85 μmol). The reaction mixture was stirred vigorously for 19 h and then acidified (10% citric acid) and filtered through a plug of celite and washed with EtOAc. The filtrate was transferred to a separatory funnel and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to provide the title compound.

Source