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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 722274Generated: October 31, 2026

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl ((1R,2R)-2-{[(5-chloro-1H-indol-2-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)carbamate

https://huagongshe.com/reaction/722274

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantDiisopropylethylamineHCID 81531—
Reactant5-Chloro-1H-indole-2-carboxylic acidHCID 82693—
Reactanttert-butyl ((1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl)carbamateHCID 11299644—
SolventDichloromethaneHCID 6344—
Producttert-Butyl ((1R,2R)-2-{[(5-chloro-1H-indol-2-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)carbamateHCID 5874249194%

Reaction Steps

5-Chloroindole-2-carboxylic acid (391 mg, 2 mmol), tert-Butyl [(1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl]carbamate (497 mg, 2 mmol), DIPEA (350 μL, 2 mmol) and HOBT (270 mg, 2 mmol) were dissolved in DCM (10 mL), stirred for 5 mins, then EDCI (479 mg, 2.5 mmol) was added and the reaction stirred for 3 hours. The volatiles were removed by evaporation under reduced pressure, EtOAc (25 mL) was added and the organic solution washed with water (2×10 mL), brine (10 mL), dried (MgSO4) and the volatiles removed by evaporation under reduced pressure to give the title compound (800 mg, 94%) as a pale brown foam.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07138415B2
Source datasetuspto-grants-2006_11
ORD IDord-52b5a72d11eb41d6b29f8c82809af1d9
Source noteuspto-grants-2006_11