rac-(1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acid → (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

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Reaction Steps

To a suspension of the Wang resin-supported racemic-(trans)-2-(4-nitrophenyl)cyclopropanecarboxylic acid (XIIc) in N-methylpyrrolidin-2-one (NMP, ˜15 ml/mmol) was added tin chloride dihydrate (15 equiv.). The mixture was shaken for 67 h and then filtered. The product resin was washed with NMP (×2), DCM, dioxane, dioxane-water (1:1×2), water (×2), dioxane-water (1:1×2) dioxane (×3), DCM (×3), methanol and ether, then dried in a vacuum oven at 40° C.

Provenance & Evidence