Benzyl carbazate → N'-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonyl)-hydrazinecarboxylic acid benzyl ester

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Reaction Steps

To a solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid (2.2 g, 9.9 mmol), hydrazinecarboxylic acid benzyl ester (3.38 g, 20.4 mmol) and DIPEA (2 mL) in DCM (50 mL) is added TBTU (3.2 g, 10 mmol). The mixture is stirred at rt for 20 h. The mixture is diluted with Et2O (200 mL) and extracted with 1M aq. NaOH (3×50 mL) and 1M aq. HCl (2×50 mL). The organic phase is dried (Na2SO4), filtered and evaporated to give crude N′-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonyl)-hydrazinecarboxylic acid benzyl ester; LC-MS: tR=1.01 min, [M+1]+=371.25.

Provenance & Evidence