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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 413345Generated: October 29, 2026

Tetrahydrofuran → 4-[[(6r,7As)-2-(2-bromophenyl)-hexahydro-6-hydroxy-1-oxo-3h-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile

https://huagongshe.com/reaction/413345

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantDiisopropylethylamineHCID 81531—
ReactantTetrabutylammonium FluorideHCID 2724141—
ReactantN-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)carbodiimideHCID 12043083—
ReactantHydroxy l-proline methyl ester hydro chlorideHCID 21063054—
SolventMethanolHCID 887—
Product4-[[(6r,7As)-2-(2-bromophenyl)-hexahydro-6-hydroxy-1-oxo-3h-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrileHCID 988874678%

Reaction Steps

The standard procedure was followed using N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)carbodiimide (102 mg, 0.24 mmol), diisopropylethylamine (60 μL, 0.26 mmol), hydroxy L-proline methyl ester hydro chloride (44 mg, 0.26 mmol) and TBAF (0.29 mL, 0.29 mmol) in THF (2.5 mL) and methanol (0.1 mL) to give 80 mg (78%) of 4-[[(6R,7aS)-2-(2-bromophenyl)-hexahydro-6-hydroxy-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile as a tan powder. MS(EI) m/e 427 (100 (M+)).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06566387B1
Source datasetuspto-grants-2003_05
ORD IDord-53f9b60870fa40c6ad66cea13b863a50
Source noteuspto-grants-2003_05