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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2221319Generated: November 3, 2026

Diisopropylethylamine → benzyl (2S)-1-[(2R)-2-{p-toluenesulphonyloxy}propionyl]-2,3,4,5,6,7-hexahydro-1H-indole-2-carboxylate

https://huagongshe.com/reaction/2221319

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantBenzyl (2S)-2,3,4,5,6,7-hexahydro-1H-indole-2-carboxylateHCID 11253898—
Reactant(2R)-1-Chloro-1-oxopropan-2-yl 4-methylbenzene-1-sulfonateHCID 12761566—
SolventDichloromethaneHCID 6344—
Productbenzyl (2S)-1-[(2R)-2-{p-toluenesulphonyloxy}propionyl]-2,3,4,5,6,7-hexahydro-1H-indole-2-carboxylateHCID 86607359—

Reaction Steps

Introduce into a reactor 200 g of benzyl (2S)-2,3,4,5,6,7-hexahydro-1H-indole-2-carboxylate and 1.5 litres of dichloromethane, and then bring the temperature of the reaction mixture to 0° C. and add 201 ml of diisopropylethylamine, followed by 202 g of (1R)-2-chloro-1-methyl-2-oxoethyl p-toluenesulphonate. Subsequently, bring the mixture to ambient temperature. After stirring for 1 hour at that temperature, wash the mixture with water. The solution of benzyl (2S)-1-[(2R)-2-{p-toluenesulphonyloxy}propionyl]-2,3,4,5,6,7-hexahydro-1H-indole-2-carboxylate so obtained is used as it is in the following Step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07368580B2
Source datasetuspto-grants-2008_05
ORD IDord-a758033eca4f456e9f4b0171064cc115
Source noteuspto-grants-2008_05